Why Empathy Is the Secret to Leading Through Tough Decisions

Leadership isn’t for the faint of heart. It’s difficult by design. At its core, leadership is about making decisions—many of them difficult, and some of them unpopular. A leader must often choose a path that not everyone agrees with, weighing what’s best for the organization against how it might impact individuals. And that’s part of the job: to make the tough calls even when others might not fully understand or support them.

But here’s where great leaders distinguish themselves. While decisions must be made, and action must be taken, how those decisions are made—and how people are treated along the way—defines the legacy of a leader. This is where empathy comes in, not as a soft skill, but as a strategic advantage.

The Case for Empathy in Leadership

Empathy is the ability to see the world through someone else’s eyes. In leadership, it means taking the time to understand what your people are experiencing—even when you can’t change the outcome. It doesn’t mean avoiding hard decisions. It means making them with humanity.

Empathy builds trust, and trust builds alignment. And alignment is what allows an organization to move forward, even when times are uncertain.

When I think about leaders I admire, either through reading about them, and in many cases having had the privilege of working for many great leaders I’ve observed the following commonalities:

  • Average leaders make decisions and get results.
  • Great leaders do the same—but in a way that brings people along with them.

An average leader explains the “what.” A great leader also explains the “why.”
An average leader gets compliance. A great leader inspires commitment.
An average leader operates with authority. A great leader operates with authenticity.

Few would argue the impact of Abraham Lincoln’s leadership during the Civil War. He made some of the most difficult, divisive decisions in American history. But he led with deep empathy—even toward those who opposed him. Lincoln’s famous quote, “Do I not destroy my enemies when I make them my friends?” reflects his belief in finding common ground in the face of division. That demonstrates incredible empathy capabilities which in turn became the mark of his greatness.

The Leader’s Critical Obligations

Whether you lead a handful of people or thousands, leadership brings obligations—not just to your business, but to your people. Each day I do my best to:

  1. See People, Not Just Roles
    Behind every title is a human being with dreams, fears, and stories. A leader’s job is to understand what makes people tick, and to help them thrive—not just produce.
  2. Create Psychological Safety
    Innovation, honesty, and growth all begin with safety. People must feel safe to speak up, take risks, and be vulnerable without fear of blame or retribution. When teammates act fearlessly and with vulnerability, not afraid to make a mistake, you know you’ve done this well. Fail fast, fail forward.
  3. Champion Common Ground
    When opinions differ—and they will—a leader must become the bridge. Finding shared values and uniting people around a common mission is a leader’s superpower.

Empathy Is Not Weakness—It’s Strength

Empathy doesn’t mean avoiding hard truths. It doesn’t mean being a push-over, or weak. It means being able to deliver difficult decisions with care. It doesn’t mean pleasing everyone. It means respecting everyone—especially when decisions don’t go their way.

We’ve all heard it—people might forget what you said, but they’ll remember how you made them feel, especially when things get tough. I’m definitely not perfect at this, but I try to keep it front of mind every time I make a decision. It’s what I strive for every day—even when I don’t get it perfectly right.

Customer Success:  5 Requirements to Creating Value in Every Client Interaction.

 

Today’s buyers are overwhelmed with data points, reports, metrics, and an avalanche of nonstop news whether its from traditional networks, cable news, or social media.  Points-of-view are as infinite as the number of stars in the universe…or are they?  In a world dominated by countless Customer Success models I continue to observe just how complicated we’ve made some basic human interactions, and just how little value some of these interactions deliver.

 

Great Customer Success interactions require 5 crucial elements:

 

  1. It all starts with a clear customer success statement as articulated by the customer.  What does success look like?  When we meet 3 months from now, what would have to be true for you to say this engagement is a success?
  2. A strong understanding of general market conditions (macro), and the ability to connect those dots to your customer’s situation, this is what I call “pulling the thread all the way through”.  It requires solid structured thinking skills.  The ability to define a problem, understand the cause, and create a solution that reduces or eliminates the problem. 
  3. Ability to create insights – combining a fact with an implication or point-of-view,
  4. Strong EQ skills that allow you to connect/relate to your customer/buyer on an emotional level,
  5. Storytelling skills

 

I’m sure someone, somewhere is saying, “yeah, but what about…”, or “Customer Success is so much more than these 5 things…”, or “you don’t know my industry, it’s so different than any other industry…”

 

What does this look like in our daily lives?

 

Think of someone in your network you respect and learn something from every time you speak to him, or her, who would it be?  What characteristics does he/she possess? I’d suggest they made your list because they are proficient at all 5 of these competencies and perhaps expert at some of them.  Certainly, you wouldn’t offer me a name of someone boring who lacks details, confidence, or a clear point of view.  No.  Instead, you’d share a name of an individual that you hold in high regard, or perhaps even aspire to be like.

 

Once basic human needs – food, clothing, shelter, safety – are satisfied, you transition to next-level needs which include the need to be heard, understood, validated, and the ability to succeed.  These next-level human needs address both self-esteem and self-actualization.  Said differently, we all desire confidence and ultimately the need to be seen by others as being successful – that we’ve reached a position of respect, or sought-after expertise.

 

Tying it all together…

 

Customer Success Managers (CSM) are entrusted with managing, and growing client relationships.  The CSM has one of the most challenging roles in an organization as they walk the tight rope between Sales, Service, Marketing, Operations, IT, HR, Finance, and virtually any other functional area that touches the client with the potential of creating an experience be it positive or negative. Understanding macro-economic conditions does not mean going back to school to obtain an Econ degree.  As a result of the diversity of a CSMs interaction with a client it’s imperative for him/her to understand how macro conditions affect the customer’s business.   This doesn’t require an advanced education but rather some basic structured thinking, discipline and commitment.  This is the ability to define a problem, understand what causes the problem, and finally creating a solution(s) that addresses the problem.

 

Client Success Managers (CSM), need to have a general understanding of the market conditions.  What’s happening in the market?  How are interest rates moving?  What’s happening with employment numbers?  How is inflation trending?  Where is consumer confidence?  With one or two apps on your phone you can stay abreast of every major macro metric in real time…in less than the time it takes to sip a cup of coffee.  It requires the discipline to build that habit into your day.  According to an October 2023 survey by Statista, people on average spend 2.5 hours per day on social media.  Using 3 minutes of that time every day to understand market conditions doesn’t seem like a huge change in behavior…but it can be if you let it…you’ve got to commit.

 

I often use the phrase, “pulling the thread all the way through.”  This means, having the capability, or skill to understand these conditions and pull the thread all the way through to how these macro conditions affect your customer through storytelling.  Doing this allows you to clearly define the problem your customer is currently facing, or about to face, and be able to communicate this to them in a way that is both articulate and confident.  Storytelling is not fiction, nor is it fear mongering.  Storytelling involves understanding your client’s current situation, the inputs that affect the situation, and what possible outcomes may exist depending on the actions taken.  Effective storytelling can be summed up in the ability to take multiple inputs and synthesize them into a story that captivates, creates intrigue, and ultimately causes action.  Storytelling is not about scaring the client into taking the action you want, but instead is about causing the client to stop, think, ask questions, and genuinely ponder the possibilities the CSM has presented.

 

Creating insights are something many CSMs struggle to do.  Keep in mind, an insight is combining a fact with an implication, or point-of-view.  A fact could be where current mortgage rates stand, or the current rate of inflation.  An insight would be how a change, up, or down, in that rate could affect your client and what the implication would be in either scenario.  This is a learned skill.  It doesn’t just happen.  Your CSMs need to study macro conditions, practice formulating insights, and role play with sales management in order to improve their effectiveness with their client engagements. 

 

The days of “objection handling” are done.  These old school sales tactics often rely on one’s ability to out-talk, or through smoke-and-mirrors, overwhelm the buyer.  I always disliked old-school objection handling.  Too much emphasis was placed upon having quick come backs, slick words, and one-liners.  Memorize these 3 responses and you’re golden.  Unfortunately, this approach is why Sales as a whole is often viewed in a negative light.  People are reluctant to meet with a salespeople and many salespeople don’t like to tell others they are salespeople.  How can we change this perception?

 

Being insightful is how you earn your customer’s time – their most precious resource.  People are only willing to invest their rarest of resources (time) with those that they can learn something from, and who make them feel validated.  So why is this so difficult?  Why do client engagement professionals still rely on old school objection handling?  Well, I’d suggest it’s because being able to provide real insights and value requires a full-out dedication to learning and understanding market conditions versus memorizing 3 great come-backs when a client raises an objection. 

 

Still today, too many salespeople subscribe to the nonsense of Sales ABC – Always Be Closing.   If this is happening in your company, I’d suggest this is a failure of leadership not leading…not teaching.  If leaders don’t raise the bar and expect a higher degree of business acumen, then their respective teams will fall back upon these ABC rules because they have nothing else.  Leaders need to lead.  This means leaders need to teach.  Further, this means leaders need to get more comfortable with being vulnerable.  Most people dislike role playing as much as they dislike public speaking, leaders included…perhaps more so.  However, role playing is a crucial element to improving your ability to take facts, formulate insights, and tell a story that leads to action, all in real-time.  Role playing for salespeople is the equivalent of a quarterback taking snaps under center at the line of scrimmage.  Defenses unfold in real-time.  We all know that good judgement comes from experience, and experience comes from bad judgement.  This is why professional sports teams practice, practice, practice.  The coach creates and environment that allows for real-time judgement based upon real-time changes to the scenario…all with the goal of making these bad judgements in the safety of a practice versus a real game.  As leaders it’s our job to create these types of learning environments for customer success managers to hone their skills.  It also means the leader must risk a wonky role play in front of the team.  No one has all the answers, but the best leaders, are okay with getting it right versus focusing on being right.

 

In conclusion, customer success is about having a clear success statement articulated by the customer.  Great CSMs will provide a blend of facts and insights that address their customers problems which result in earned trust and respect.  These CSMs take chances, formulate insights, role play their delivery, and embrace the outcomes as their own.  They are the game changers, the difference makers, in achieving outstanding customer success.

 

 

 

 

 

 

 

 

 

 

 

Choosing the right Chief Revenue Officer

Recently, I attended a webinar sponsored by Private Equity CXO.  The topic of the webinar was PE Strategy for Revenue Growth; CROs and Value Creation.  Presenting in the webinar were several Private Equity professionals sharing their insights on the impact that having the right Chief Revenue Officer (CRO) can have on an organization’s success.

Let me first say that the webinar overall reinforced my personal experiences and beliefs throughout my career as both a GTM consultant and a CRO with experience working with companies ranging in size from $50M to >$6B in annual revenue.  However, the webinar got me thinking about the challenges involved in finding the right CRO, the process that most private equity firms use to recruit CROs, and the end result…disappointingly low success rates as supported by comments in the webinar as well as in other datapoints I’ll present shortly.

While I could write pages summarizing the content of this webinar relating to how CROs should, or could create value, I will instead focus on one critical topic discussed by the group…finding the right CRO.

Herb Brooks, the famous coach of the United States 1980’s Men’s Gold Medal Olympic Hockey team, has one of the best all-time quotes and probably my personal favorite.  As he was assembling his team, he was asked why he didn’t choose this player or that player because “they were the best”.  Herb confidently, and with unwavering conviction replied, “I’m not looking for the best players, I’m looking for the right players.”  This philosophy will serve as my anchor for why the right CRO may look quite different from the best CRO. 

I believe Coach Brooks could not have been more spot-on.  While I’m sure this comment will strike a chord with some, I stand by the belief that skill is much easier to teach than attitude, let alone chemistry, as it relates to team dynamics.  A Harvard Business Review study showed that 44% of a company’s market value is attributable to its CEO’s reputation. This study further defines reputation as a combination of 3 key emotional intelligence characteristics including humility, visibility, and persuasiveness.  One may conclude that some portion of a CEO’s reputation is a direct extension of the CEO’s executive and senior executive leadership team if you believe that a company’s culture is the sum of its parts.

Throughout the webinar the conversation often returned to the importance of the CRO’s team building capabilities, and leadership skills required to build a sustainable high performing culture. 

From an operator point of view, I would say that while a new (and even existing) CRO certainly has the responsibility to lead and effect change in an organization, a new CRO especially needs to understand the existing culture that he/she is walking into, the runway in front of this them (timing expectations), and as mentioned in the webinar, a list of the “jobs to be done” – the critical items that must be completed within the next 12 months.  Measure twice, cut once, applies to walking into a new role for both sides of the relationship – CRO and private equity partners.  The greater clarity provided at the onset, the greater the likelihood of success and perhaps fewer missed expectations. 

I strongly believe that the “right” CRO has both a track record of successes and failures.  I’m always leery when I speak to any executive-level candidate who positions themselves as having made perfect decisions.  Perhaps I’ve been blessed to work for leaders like Scott Cook of Intuit, who famously pushed our management team to make more mistakes – fail fast – as a barometer for the speed of innovation.  If you’re not pushing boundaries, you’re not growing, you’re not evolving, you’re simply presiding over something that’s fairly vanilla, and hence replaceable.  Basic, or as I like to call them, cut-and-pasted tactics might work when the waters are smooth, but absolutely go out the window when faced with gale force winds that may include a tight job market, raging inflation, or a pandemic that shifted the norm on how we get things done in business. 

A status quo leader, not battle-tested by building and failing, decreases your probability of success and produces a lesser amount of value creation.  It’s just as important to know what not to do, then knowing what the right thing to do is, as both include countless variables, known and unknown.

Case studies or homework assignments are great, but here’s where I slightly divert from the consensus shared on the webinar.  In my own personal experience, focusing on the difficult questions to ask during an interview, combined with an Up-Down-Sideways reference check is another way to gauge the probability of success.  Some folks have a talent to write, research, and/or problem solve in a controlled environment, but rarely do we operate in controlled environments, and case studies and homework assignments are just that…controlled environments.   

In fact, I’d suggest that many sales leaders would have failed the case study in 2008-2009 during the GFC, or during the COVID pandemic.  The test of a strong leader lies in his/her ability to consume information quickly and being comfortable with operating in ambiguity.  According to Zippia, the average age of a Chief Revenue Officer is 49 years old.  When combined with a datapoint from Salesforce indicating the average tenure of a CRO is right at 2 years, you begin to understand why the concept of battle-testing is so important over a variety of different environmental factors relative to creating and sustaining high performing teams.   One could argue that even as case studies and homework assignments have become the norm for recruiting CROs, the success rates are discouragingly low at less than 2 years.  Why is that?  Here I’d suggest that what’s often missed is the softer, and perhaps more difficult skills to assess that include EQ (some of the items from the HBR study), charisma, and empathy, all of which are critical leadership qualities to establishing and maintaining high performing teams. 

As Stephen Covey famously said, “people don’t care how much you know until they know how much you care.”  A leader showing up as the smartest person in the room likely will result in a team that tries to distance itself rather than embrace.  Hence why EQ is so important when selecting a new CRO.  And, with the average tenure of a CRO being 2 years, one possible conclusion that might be drawn is that too many know-it-alls show up day one on the job versus showing up with a learners mindset. 

Of course, the right mix between EQ and IQ is critical.  And while I referenced the criticality of some of the softer skills above, I also want to be clear that an effective CRO must have the passion and capability to deliver tangible tools to the teams they lead.  I have written countless playbooks, personas, and ICPs for the teams I’ve led throughout my career as a CRO.  I study data, identify trends, create hypos to prove/disprove.  I spend a great deal of time in the field with sales professionals running these plays and adjusting them accordingly, perhaps another carry-over from my experience at Intuit with Noel Tichy’s famous “teach, learn, teach” model underpinned our day-to-day operating rhythm in the business.

Often, I see CROs rely much too heavily on outside consultants (I was one of those), to do this type of work.  Why?  Because they either are not close enough to the business to know, or in the worst cases feel that the level of in-the-weeds work is beneath them.  This, however, is exactly the work that moves the needle by building sales effectiveness, team spirit, and a high performing culture where teams recognize that their Sales leader is sleeves-rolled-up, capable, competent, and credible. 

It was mentioned several times during the webinar private equity’s desire for predictability.  Delivering a “flash-in-a-pan” result is easier than producing consistent results over time.  Again, this is why it’s critical to be clear about what is required within the first 12-month period and what resources are available to accomplish those requirements.  The resource discussion is yet another topic that is deserving of its own thought leadership piece.  For now, here’s a simple way to illustrate the importance of having the right resources…

As someone raised in a musical family, and having played drums for many years, I consider Neil Peart to be arguably the best drummer of all time.  So, was it the 54-piece drum kit that made Neil sound so incredible?  Or was Neil’s raw talent such that he’d sound good no matter how many drums he had at his disposal?  While I’d seen Peart amaze enthusiasts on a regular 4-piece Jazz set, the sounds and complex rhythms he played on 54 pieces simply amped things up a notch.  He had the resources to transcend being great to being the greatest.  Now, drop in Phil Collins behind Peart’s 54 pieces.  Would Collins, another great, sound equally impressive?  Or does it suggest that resourcing wouldn’t matter, and that Collins would just “know” how to play, what to play, and when to play it?  As a reference point, Phil’s typical set is (was) a 10-piece kit.  Regardless, it’s clear that talent, plus resourcing, equals output.  The key to success is understanding what that specific talent requires, relative to resourcing, to produce the expected or desired results.

Back to the CRO thing, a CRO must also have the ability to look at data and make inferences…quick assessments of a situation.  Deductions usually come when deeper analysis is done, and oftentimes, the ability to do a deep dive is limited by a company’s systems, platforms, access to the data itself (perhaps it’s never been captured historically), or not having the analysts (talent) available to do such work.  This leaves the CRO in the position of either taking no action as they become paralyzed by fear of making the wrong decision, or the opposite extreme, making knee-jerk decisions as they quickly fire from the hip.  This area of CRO skill must also be contemplated when thinking about culture, timeframes, and expectations.

Finally, the relationship the CRO has with his/her owners/investors cannot be underestimated relative to performance.  Are the company’s owner enthusiastic supporters?  Are they impatient investors who have gone through a series of failed CROs leading them to bring high levels of doubt or skepticism into any new relationship?  Does the CRO have solid chemistry with both the CEO and CFO?  It has always struck me as odd that I’ve personally never interviewed with a CFO while being recruited for the top Sales chair, yet my personal relationship with a CFO, as a CRO, is perhaps equally important if not more important than the relationship between a CEO and CRO.  There’s a ton there to unpack as a topic – the relationship between CRO and CFO – that opens the door for future thought leadership content.

In summary, finding the right CRO begins with an accurate assessment of the future of the asset.  Where are we in the hold period?  What has the last 3-5 years of organic growth looked like for the company?  What’s the tenure of the team?  Is it a complete build, or rebuild?  Is there a VP of Rev Ops in place, and further, how strong is that person relative to all aspects of analysis and GTM tech platforms?  Do any of the CROs previously-built-teams still exist?  Can the CRO demonstrate an example where he/she groomed and promoted their replacement, and where and how is that replacement fairing today?  With the average age of a CRO being 49, what was he/she doing during the dotcom bust, the GFC, the pandemic, and most recently our current period of high inflation and stifling borrowing rates?  Can the CRO candidate comfortably articulate key learnings from each of these periods and demonstrate how those learnings enabled them to better navigate through the subsequent challenges or crises?  What tangible examples can the CRO point to as evidence of something they built new, as a response to their own evolution of thought due to their experiences?    

In choosing the right Chief Revenue Officer, it’s essential to recognize that leadership is not just about past successes, but about the ability to adapt, evolve, and thrive in an ever-changing business landscape. The true measure of a CRO lies in their capacity to turn challenges into opportunities, ensuring that their experiences become the cornerstone for future growth and innovation.

20 Objectives For All Chief Revenue Officers

  1. Be a continuous learner – what got you into the CRO role won’t keep you there.
  2. Create a culture of innovation – willingness to try new things without the fear of failure.
  3. Demonstrate teamwork and camaraderie – people will watch and observe your behavior before they act.
  4. Focus on the people – this means getting to know your colleagues beyond their quotas.
  5. Be authentic – this equals consistency and predictability. Wild mood swings are often due to people transitioning from their “real” self to their created façade.
  6. Be vulnerable – show you’re human, it’s okay.
  7. Confront reality – denial wrecks your credibility. Quotas are huge, don’t act like they’re no big deal.
  8. Provide a path to success – it may be a difficult path but a path none the less. Remember, the leader’s job is to provide the vision…the possibilities.
  9. Be honest – shoot straight, share what you can, not only what you must.
  10. Always have an active ear – listen…actively. People want to know how much you care before caring about how much you know.
  11. Never surprise your boss – understand what’s important to the CEO and how/when to best communicate.
  12. Be deliberate in your actions – an environment of uncertainty is a byproduct of hedging bets. Your team will know if you’re not all in.
  13. Be kind – nothing in this job should justify taking someone’s dignity.
  14. Be gracious – say thank you. Give credit and recognize people consistently.
  15. Look for the good – every day find a good deed, or success from a colleague, and then share it.
  16. Know your numbers – where are you this month to quota, next month, and quarter standings.
  17. Know your business – what external factors may arise to get in the way of achieving your goals and those of your colleagues?
  18. Always be planning – “In preparing for battle I have always found plans are useless, but planning is indispensable.” ~ Dwight D. Eisenhower
  19. Stay fit – CROs tend to be the heartbeat of a company. Work hard to have and maintain a healthy heartbeat.
  20. Always, always, remember (and thank) those who helped you arrive – family, friends, former bosses, mentors. No one gets to where they’re going totally alone

Leaders are not born, they’re developed

I recently had dinner with one of my top sales people in San Diego this week and the conversation got around to whether people are born as natural sales people, or leaders.

I’ve never been a believer that people are born into a specific life path. What I believe is that each of us is born with a set of talents, capabilities, and competencies. We are all born with a specific attitude as well. A mindset, a glass half full, versus half empty thinking. A skeptic, an optimist, or pragmatist.

Here’s where the conversation gets fun. Believe it or not there was an interesting life lesson that has stuck with me for years from a rather unexpected movie – RAMBO III. In the movie the character of Colonel Troutman gives a pep talk to John Rambo. He tells the story of a sculpture who finds a perfect stone. He drags it back to his workshop and creates an incredible statue. When his friends compliment him on his creation, he says, he didn’t create anything. The statue was always there…he just chipped away the small pieces.

We are all born with natural talents. Some are blessed with athletic abilities, others with analytical strengths, others with caregiver strengths. The difference between those that achieve their full potential versus those who don’t, is finding a mentor(s) who helps validate and provide direction for your unique set of skills.

What if there was no Earl to Tiger Woods? What if no Joe to Michael Jackson? What if no Kurt to Michael Douglas? There are thousands more of these examples of folks who are not in the limelight but succeeded because they benefited from someone who recognized their talents and provided direction and encouragement. I’ve been incredibly blessed to have had a number of bosses throughout my career who have guided, counseled, and encouraged me to embrace my skills, take chances, and stretch. Without them, I am certain I would not have accomplished what I have thus far. And while I’m now considered “middle age”, my need for their input, guidance, and counsel still remains strong. Being a continuous learner never stops…until the heart does.

So what if you don’t feel like you have a person like this in your life? What do you do to find someone to fill this gap? The answer is easy. Look around. That person is probably closer to you than you think. It could be a spouse, partner, boss, friend, someone at the gym, someone sitting next to you on a plane. In fact, my love for American history was born on a flight I was on in 2004 when I met a gentlemen who asked me what types of books were my favorite to read. Foolishly I said none. He said, how can you spend so much time on a plane and not read. He told me I was missing all kinds of opportunities to expand my thinking. When we landed he gave me a book that became the catalyst for creating my voracious appetite for reading. That book was called His Excellency on George Washington. I can’t count the number of books I’ve given away over the years to people who I just met in similar situations. You never know who, or how you can impact the life of a stranger for the better. It’s incredibly heartwarming and fulfilling.

Life lessons are everywhere. Sometimes you just need to put down your phone, take out your ear buds, and just be…be present. Take an inventory of all the things you’re good at. Jot down what you like to do. Assess the crowd you hang with and identify a few people to approach to help you clear away those stones. Remember, the statue is always there…it’s just how badly you want to chip away at the stones to show your uniqueness and value to the world.

How Sharing Can Accelerate Results

In today’s rapidly advancing digital age, information has never been easier to access. We shop for clothes, cars, computers, and countless other consumables and services through the internet. We research our customers, competitors, future employers and employees, and bosses. We share our experiences and opinions about banks, hairdressers, mechanics, and restaurants on sites like Yelp, Facebook and Google. In fact, by the time you finish reading this blog, more than 1 million posts will have been made on Facebook (assuming you can finish this in 2 minutes or less).

With so much information, so quickly accessible, why do businesses still operate in silos? Why do management teams, and executives, feel compelled to withhold information from their teams? Are there still people that believe in Jack Nicholson’s position in A Few Good Men? Perhaps some might not be able to handle the truth but most are far more capable than you may think. In fact, if you consider real-life General Stanley McChrystal, in his book Team of Teams, he talks about transforming the U.S. Military from a command-and-control operation to a “shared consciousness” where there is an organization-wide “understanding of the whole.”

So why do executives hold back? Why do they covet information at all? The answer is FUD – Fear, Uncertainty and Doubt. Fear of embarrassment, uncertainty of reaction, doubt in the character and tenacity of the people on their teams. Harold MacMillian said, “A man who trusts nobody is apt to be the kind of man nobody trusts.” This couldn’t be more true.

Sharing for the sake of sharing is a waste of time and effort, however, sharing for the sake of establishing trust is an accelerator of positive results. How do can you tell if sharing is real? If the information the leader is sharing is sensitive, in that it makes him vulnerable, he’s sharing. If the information is sensitive, in that it may make the company vulnerable, she’s sharing. If there is any level of personal, professional, or company risk, this qualifies for real sharing. When real sharing is being demonstrated, a culture of trust can begin to develop and teams begin to form. A leader who shares real stuff is confident, comfortable being vulnerable, and willing (and interested) in learning. Those are the leaders people seek to follow.

Still think sharing is a crock? If you need further evidence that sharing can accelerate growth, look no further than Berkshire Hathaway which currently holds the title as the highest priced stock on the NYSE at more than $320,000 for a BRK-A share as of this blog post. If you, like me, believe that sharing is a critical ingredient to building trust, consider the words of Berkshire’s Charlie Munger, “By the standards of the rest of the world, we over trust. So far it has worked very well for us.” It certainly has.

How much courage do you have to start sharing?

12 Things Great Leaders Do Daily

McChrystal

By definition a leader is a person who leads or commands a group – at least that’s what Professor Google says.  My definition is a bit different.  Who wants to be commanded?  Sure there are times, situations, and circumstances when being in command is required.  Directing, ordering, and controlling are verbs that often come to mind when we think of leaders.

Just about anyone can be taught to do these things.  Just about anyone can dish orders, direct others, and attempt to control.  Many “leaders” regardless of training can do this for some period of time before being discovered as ineffective.  Great leaders however, take a different approach.  These leaders must do all the directing, ordering, and controlling as previously mentioned but it’s how they accomplish these things that set them apart.

Great leaders are great because they:

  1. Understand how to empathize
  2. Effectively communicate their vision
  3. Ask great questions, deep questions that provide insight
  4. Act in their own authentic way, not trying to be someone else
  5. Adopt a beginners attitude
  6. Surround themselves with people smarter than they are
  7. Spend time on self-reflection, how they operate and the result produced
  8. Network and connect with others to learn
  9. Ask for, and accept help when needed
  10. Lean on mentor(s) for coaching and perspective
  11. Roll up their sleeves, never asking others to do something they haven’t or wouldn’t do themselves
  12. Inspire others through their words, actions, and behaviors

So start today with some self-reflection.  What are you doing?  What do you spend most of your time on?  How do you interact with those around you?  What’s the reaction of others when you walk in a room, speak during a meeting, engage with others in a break-room?  Consider this list and strive to embrace each one in a genuine way and you’ll find your results improve in a timely manner.

Be a Tour Guide Instead of a Sales Person

 

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In 2015 I took my first trip to Yellowstone National Park.  To be honest it wasn’t my first choice, but it was solidly in my dad’s bucket list and so we made it a “guys” trip.  Three generations of DeRosa’s (father, son, grandson) traveling to where the buffalo roam, to see exploding geysers, breath-taking views, and to take in the simple beauty of the land.

Of course, the sales and marketing geek inside of me looks for every opportunity to observe, study, and ponder how each experience plays into how people make buying decisions.  Yes, even at Yellowstone I was on the prowl for insights into how sales people can better connect with the buyers journey.  Our Yellowstone tour guide unknowingly provided a powerful example in navigating the changing scenery of the buyers journey.  But first a little context…

If you’re in Sales, or any position charged with hitting a revenue number, you’ve got to sell.  You need to find buyers, and you need to sell them.  Sell them as much as you can, as quickly as you can, to reach your number, celebrate briefly and move on to the next.  Right?

WRONG!

Buyers have become increasingly sophisticated whether buying a pair of shoes, or selecting a payroll provider, or choosing Tom Ford over Hugo Boss.  If you think selling hard, and selling fast is your best chance of success you may want to consider a different career.  Today’s buyer wants to be courted.  They want to feel special. They want to feel important.  They want to believe the option they have chosen is the best option for their need.  Notice I didn’t say the buyer wants to have confidence in the solution you sold them.  No.  They are not to be sold.  They are doing the buyer.  They want you to be their tour guide.

I watched as Kylie, our tour guide welcomed us to a small group tour setting out to see Yellowstone in all its majesty.  Her welcome was warm and genuine.  She was quick to point out the creature comforts we probably would need for this journey.  Blankets, water, soft drinks, snacks, distance between rest stops.  She had anticipated our questions and addressed them before they were asked.

As we started our journey from the Grand Teton’s into Yellowstone, Kylie provided a history of both parks in a way that only a master-storyteller could do.  Her story was highly engaging, edge of your seat, filled with suspense.  She educated us on the wildlife ecosystem and how everything was interconnected.  I’m embarrassed to say I probably learned everything I know about biology and the circle of life from this tour.  Up to this point in my life I hadn’t taken time to think about how life and nature were interconnected. She led us on this journey of enlightenment through her personal passion for the landscape and wildlife within these two parks. It was amazing. In fact, so much so, that we embarked on a second tour a couple of days later with a different focus, in a different part of the park.

I’ve often thought about my experience on this Yellowstone tour.  I’ve thought about how I was educated in a way that allowed me to fully grasp the concept of a wildlife ecosystem.  I think about how my interests in conservation have since grown as a direct result of this new knowledge.  I ponder the impact personal passion has on the transfer of knowledge.  I do believe that if Kylie simply read a script, or ran through the motions, I would have left Yellowstone feeling quite different…less connected.  Her passion created questions of my own.  Her stories have become remarkable memories for me, my father, and my son.

As a revenue leader it is important to have a true passion for what you do.  It’s not enough to be a VP of Sales.  Kylie could have been a tour operator for a double-decker bus in Manhattan, but it wouldn’t have served her passion.  You’ve got to have passion for what it is you’re selling.  What is the ultimate purpose for what you do, what your product does, what improvement it makes in the buyers life.  Too many people are occupying positions for a paycheck, not really believing in what it is they are selling.  We’ve all done it.  The problem is, your buyers can spot a scripted seller miles away and today they vote with their shoes by either walking toward you or walking away.

View yourself as your buyer’s tour guide.  Anticipate their questions and provide answers before they ask.  Make the journey as comfortable as possible.  Be warm, be kind, be generous with your time.  Study and learn…I mean really learn about what it is you’re selling.  If you can’t get excited or enthused about it find a new product to sell.  Your goal is to help your buyer through this journey at their pace, not yours. Be the best sales tour guide you can be.

5 Things To Prepare For Before Mapping Your Buyers Journey

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It doesn’t matter if you’re a start-up, or a business that’s been around for 50 years, your buyer has changed. He changed last month, last week…he even changed yesterday. Thanks in large part to Moore’s Law (technology doubles every two years), we know that his access and availability to information is endless.  Today’s buyers are more connected, more savvy, more social than ever before.  In fact, it’s likely your buyer will know more about you than you know about him before you ever meet one another.  That is if you ever do meet one another.

We have all heard the statistic that 92% of all B2B purchases begin online.  That means that 9 out of 10 prospects will be checking you out well before any meeting ever comes to fruition. We also know that many sources report that at least half of the buying process is complete before the buyer ever meets a sales person.  For some companies like Amazon, Apple, and Tesla, they thrive on this disruptive buyer.  The buyer who shops at her own pace, educates herself on what she wants, with the content she wants, and from the sources she wants it from.  For other companies perhaps not as sophisticated in their understanding of this evolution…this buyers journey…the need to gain this understanding is critical.  It’s urgent.  It’s truly about survival.

To map your buyer’s journey requires time, access to customers willing to participate and answer questions, and likely the most important requirement being the business’s willingness to listen and change based upon these findings.  This is critical work, not easy, but certainly doable.  The rewards of understanding your buyers are many. The risk of not understanding your buyer is simple…irrelevance that leads to extinction.

Here are 5 things you need to prepare yourself, and your company for as you begin to map your buyer’s journey:

  1. Open-mindedness. Start this work with a beginners attitude. If we were launching today, knowing what we know, what would we say to our buyers, how would we say it, when, and where would we say it?
  2. Honesty. If your brand promise is “fast and easy” but your delivery is slow and confusing be honest about it. Guess what, your buyers already know this about you.  Resist the denial urge.
  3. Customer mindset. Our buying habits and expectations as consumers are gradually following us into our business lives. If I can buy a new computer fast and easy at home, I expect to be able to do the same thing at work no matter what product or service I’m shopping for.  My expectations for speed and ease, transcend the business experience.
  4. Acknowledgement and Acceptance. All change requires acknowledging there’s a better way, and accepting the fact that we will have to do something(s) different to achieve that better way.
  5. Action. Be ready, willing, and able to act. Some people, and businesses, are ready for a different outcome, but are not willing or able to implement the change required to generate that better outcome.  Change only happens when a different action is taken.

The age of the buyer is here.  Those who decide to align their business around the buyer will survive and thrive while those who still believe they control the sale will slowly fade away. Your job is to understand how you can best facilitate your buyers process – their journey – not your sales process. Helping and serving have become the keys to success in the age of the buyer. Now you just need to know where to help, and how the buyer wants to be served.

Sales 13 Deadly Sins

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Whether you are new to Sales, or have been selling for 30 years, a true Sales professional must always guard against these 13 deadly sins:

  1. Winging it.  Don’t be too confident that just because you know your product inside-out, and may be working for a market leader, that the buyer will simply sign on the dotted line.  Plan, focus, and prepare for each sales interaction.
  2. Judging a book by its cover.  Never assume that you know the buyer before you’ve met her.  Sure, you may have sold 100 buyers like her in the past but no two buyers are “just” like another.  Take the time to learn what’s different.
  3. Careless.  No one likes a careless person. It takes several forms from sloppy hand writing, to inappropriate dress, to bent presentations…just plain old messy.  If you don’t care, why should your buyer? Be neat. Be presentable. How you present your whole self shows the buyer your respect for yourself and for him.
  4. Being late. Don’t be late…ever.  Traffic isn’t an excuse.  Sure there’s a late plane, train, or bus.  The unexpected accident you get caught up in.  But normal traffic is not a reason to be late.  Plan accordingly.  If you’re on time, you’re late.
  5. Being uninformed. Shallow?  Ugh. People don’t want to interact with a sales person who brings nothing else to the table other than the product they’re selling. Take the time to be aware of your surroundings and world happenings.
  6. Relying too heavily on your company’s brand.  Don’t assume because you’re the biggest you’ll get the business. No doubt some companies spend huge resources on building their brand. You can either leverage it and get the sale, or assume it, appear arrogant, and lose the sale.  Earn the buyers trust…you + your brand.
  7. Not identifying all the contributors to a buying decision. Your contact may not have all the power. Too often I have seen mountains of effort placed in developing one relationship only to find there were others providing input to the buying decision I had not met, or invested in.  Know those who will be a part of the buying decision.
  8. Unadaptable, inflexible.  Don’t let your presentation, or agenda, become an anchor. Years ago my boss and I traveled together to do a presentation to a big prospective partner.  Within the first 5 minutes the buyer changed directions. Much to my boss’s surprise I ditched the presentation, adapted, and won the business due to my ability to flex with my buyer’s changing needs. Have one, but don’t become married to your agenda.
  9. Stretching the truth. Just don’t do it. Don’t lie, embellish, exaggerate.  Making promises you, your company, or your product can’t keep is a sure way to kill both your personal brand and your company’s.
  10. Competition bashing. Never badmouth your competition…even if the buyer tells you they said something bad about you. Defend it but end it.  When working for Paychex, the founder, Tom Golisano, provided a stern warning for any sales person caught badmouthing its competition. He believed if someone had to sink to that level to win the business the company probably didn’t deserve to win it in the first place.  Take the high road…always, win with respect.
  11. Knowing it all. Don’t be a know-it-all. Buyers don’t expect you to be omniscient. A little humility goes a long way in earning trust and respect.
  12. Knowing little or nothing. Invest your time to learn what it is you need to know about your company, product, and industry.  Your company can’t, nor should, do it all.  You’re responsible for your knowledge, and accountable for your results. 
  13. Talking too much.  You can learn a lot more about your buyer by asking great questions and sitting back and listening to them answer.  We demonstrate respect, caring, and professionalism by listening.  Remember, two ears and one mouth for a reason.

Let me know if you have a deadly sin to add to the list.