Do I Care?

Mitch Little read my recent post on competing to lose 80-85% of our deals and responded with something that stopped me: “Your analysis is spot on. You clearly outline how to succeed. Now how do we light that fire?”

He went further: “If people do not truly care, but only go through the motions, we will continue to actually deteriorate in outcomes.”

My first instinct was to write about how organizations need to create conditions where people care. How leaders need to restructure metrics, coach differently, and focus on quality over volume.

But the more I thought about it, I realized I was doing exactly what we always do, making it about “them.” About “our people.” About what “they” need to do differently.

The real question for each of us isn’t “do our people care?” It’s “do I care?”

Before we can assess whether our people really care, we have to first look inwards, asking that question.

What does it even mean to care?

One of the reasons we don’t talk about caring is we view it as an emotion or a feeling.  Caring isn’t a feeling. It’s engagement. It’s the depth of investment you bring to everything you do.

You can see it. It’s how a seller prepares for a meeting — or doesn’t. It’s whether a manager is actually thinking about a deal or just reviewing a dashboard. It’s whether a leader is building something that lasts or managing to the next board meeting. It’s whether the board and investors are building enduring organizations or just pursuing transactions.

Caring is visible in behavior. We demonstrate it through our engagement.  And the absence of caring engagement is visible, too.

We see survey after survey of declining employee engagement.  This means people simply don’t care.

Going through the motions that have become the default operating mode for too many of us.

This impacts all of us, from individual contributors to the highest levels of leadership.

The honest self-assessment.

Before we diagnose anyone else, we have to ask ourselves some uncomfortable questions.

• When was the last time I was genuinely curious about a customer’s problem, not as a means to advance a deal, but because I wanted to understand their world?
• When was the last time I prepared for a meeting the way I would if the outcome truly mattered to me,  not just to my forecast, but to me?
• When was the last time I pushed back on something I knew was wrong;  a bad deal, a flawed strategy, a metric that’s driving the wrong behavior,  even though staying quiet was safer?
• When was the last time I invested in someone’s development not because it was on my objectives, but because I genuinely cared about helping them get better?
• When was the last time I did something that wasn’t required, wasn’t measured, and nobody would notice if I skipped,  simply because it was the right thing to do?

If the honest answer to most of these is “I can’t remember,” then we’ve found the problem. And it isn’t “them.”

Why we stop caring  and it happens to all of us.

Most of us started our careers caring deeply. We were engaged, curious, and invested in doing excellent work. Yesterday, I spoke to a freshman at UTD’s business school.  She’s studying marketing and wanted my perspective.  She was so engaged, excited, and curious.

While we start our careers, or possibly a new job, excited and engaged, what happens?

The system taught us what to care about, and it wasn’t the work itself.

The seller learns to care about activity metrics, forecast accuracy, not getting singled out in the pipeline review. The manager learns to care about making the numbers look clean, keeping the VP comfortable, not being the one who has to explain a smaller pipeline. The VP learns to care about the board deck. The CRO, knowing their average tenure is 18 months, learns to care about quick wins and visible plays that buy time. The board learns to care about quarterly performance against plan.

At every level, the system redirects engagement away from the actual work;  understanding customers, building capability, developing people, creating something that endures.  Instead we shift toward self-preservation, system compliance, and managing appearances.

There might be a tendency to “blame it on the system,” we hear that all the time.  But we created that system. And the system isn’t doing it do us, we let it happen.

It’s a vicious circle.  We choose the safe path. We stop pushing back. We tell ourselves that going through the motions is following the process, being professional, or being realistic.  We get comfortable.

Some of us withdraw our engagement from work entirely. Not because we’re incapable of caring, but because we decided,  consciously or not, that the job isn’t worthy of our full investment.

Work becomes the thing that funds what we actually care about. Our families, our hobbies, our lives outside the office. That’s not apathy, it’s a rational choice about what we care about.

But it’s still a choice each of us makes, and we have to be honest about it.

The fear that keeps us disengaged.

Mitch made an observation: “Today’s leaders are afraid of excellence because it makes them stand out, and that is too risky. I’m not sure this is even consciously understood.”

This doesn’t just apply to leaders. It applies to every one of us.

Genuine engagement makes you visible. When you care about quality,  when you push back on a bad deal, when you insist on going deeper, when you challenge whether the current approach is working, you stand out. And standing out in an environment optimized for conformity is risky.

The seller who focuses on deep customer engagement, rather than sticking to the script. Visible. The manager who coaches, focusing on the development of her people, instead of managing dashboard metrics. Visible. The VP who tells the CRO “our win rates are unacceptable and we need to change how we operate” is risking their position. Very visible.

So we learn to compensate and “fit in.” We go through the motions.  We are  not fully checked out. But  we aren’t fully engaged either. We find the safe middle. Enough effort to stay employed, enough compliance to avoid criticism, but nothing approaching the deep engagement that produces excellent work.

Most of this isn’t conscious.  It’s a series of compromises we make. And it’s killing our organizations from the inside.

The 18-month symptom.

Nowhere is this more visible than in tenures. The average CRO lasts about 18 months. Think about what that signals to an entire organization.  The average tenure of everyone else is between 11-18 months.  A person barely is onboarded.

A leader who knows they have 18 months cannot genuinely invest in building organizational capability. That takes years. So they engage with what fits their timeline: new playbooks, reorganizations, tool deployments, quick wins they can point to. They’re going through the motions, not necessarily driving the change that matters.

And everyone sees it. When the third CRO in five years shows up with another “transformational” strategy, we keep our head down, knowing “this too will pass.”

And with individual contributors we see similar things.  If they are only going to be there for 11-18 months, why should they get really engaged?  The rational behavior is to do just enough to get by.

But here’s the harder question: is that CRO or individual contributor a victim of the system, or did they accept their roles knowing the conditions and decide to play the short game?

The answer is, Probably both. And that’s the point, at every level, we’re making choices about how deeply to engage, and then we’re rationalizing those choices as pragmatism.

Boards and investors carry this same accountability. When you evaluate leadership on 18-month cycles and quarterly performance, you’ve told everyone in the organization exactly how much long-term engagement you actually value. You’ve made the short game the only rational game.

What each of us can do,  starting with ourselves.

The temptation here is to jump straight to “what leaders need to do.” But that skips the essential first step. Each of us, regardless of role,  must decide whether we’re going to be genuinely engaged in our own work.

This isn’t about waiting for permission. It’s not about waiting for leadership to fix the system, restructure the metrics, or make it safe to care. It is about your individual choice.

Choose depth over safety in the next conversation you have. The seller can choose to actually prepare for tomorrow’s meeting,  not just review the account brief, but think about what this customer is trying to achieve and why it matters.

The manager can choose to ask “what is this customer trying to accomplish?” instead of “when will this close?”

The VP can choose to have an honest conversation about win rates instead of papering over them with pipeline volume.

None of these require system change. They require personal courage.

Reconnect with why the work matters. Not the quota. Not the forecast. Not the board deck. Focus on the actual work,  helping a customer solve a problem, developing a person’s capability, building something that creates genuine value.

If you can’t find a connection to that, you have a harder question to answer about whether you’re in the right place.

Stop rationalizing disengagement. We’re all used to justifying why we don’t go deeper. “The system doesn’t reward it.” “Nobody else is doing it.” “It won’t change anything.” “I don’t have time.”  These are true enough to be comfortable and false enough to be dangerous. They’re the stories we tell ourselves to avoid the discomfort of caring in a system that doesn’t seem to care back.

Accept that engagement is risky and do it anyway. Going deep on a customer’s problem, disqualifying a bad deal, or your VP that the pipeline is smaller but better.  These are acts of courage. They make you visible in ways that feel dangerous. Do them anyway. The alternative is a career of going through motions.

In some sense, this is a very selfish act.  Focusing on what you care about, looking at what excites and engages you, seems selfish.  But without this reflection, it’s impossible to achieve your full potential.

And this “selfishness” shapes the jobs you take, and how you conduct yourself in the job.  And there will be bad fits.  Find those that are great fits.

What leaders must do after they’ve done their own work.

If you’re in a leadership role, everything above applies to you first. Before you can credibly ask for anyone else’s engagement, you have to demonstrate your own. Your people will see through any gap between what you ask for and what you model. Immediately.

The leader who demands deeper customer engagement while running superficial pipeline reviews is telling everyone the truth about what they actually care about. The CRO who talks about quality while panicking over pipeline volume has revealed their real priorities. People don’t listen to what leaders say. They watch what leaders do, and they engage accordingly.

So the first thing a leader must do is the introspection. Am I genuinely engaged in building something that lasts, or am I optimizing for my own survival? Am I doing the hard work of understanding our customers’ world and developing our people’s capability, or am I managing dashboards and decks? Am I willing to be measured on outcomes that take longer than a quarter to materialize?

If the honest answer is that you’re going through higher-level motions, then start there. Nobody else’s engagement changes until yours does.

Once that foundation is real,  then the structural work matters.

Create the conditions where depth is possible. Fewer, better-qualified deals. Enough time for people to actually think about each customer’s problem. You cannot demand engagement while structuring work so that going through the motions is the only option. If your sellers are focused only on outrageous activity metrics, you’ve made genuine engagement mathematically impossible.

Change what you measure and celebrate. Start measuring win rates by segment, deal cycle time, no-decision rates. Celebrate a well-reasoned disqualification. Recognize the seller who went deep on a customer’s problem and changed the trajectory of a deal. What you measure tells people what you value, and what you celebrate tells people what’s safe to care about.

Ask questions that reveal genuine engagement. “What is this customer actually trying to achieve?” “Why are they trying to achieve it now?” “Why should they do it with us?” “What did you learn in that conversation that changes how you’re thinking about this deal?” When leaders ask these questions consistently, they’re giving people permission to engage at a deeper level.

Coach by engaging yourself. Sit with a seller and work through a customer’s problem together. Not reviewing dashboards. Not auditing CRM entries. Do the work of understanding a customer’s world alongside them. This requires you to be skilled enough to coach at this level, which is its own form of engagement, in your and your peoples’ continued development.

Commit to a timeline that makes engagement possible and preferable. If you’re leading on an 18-month mental clock, everyone knows it. If you’re building for the long term, investing in capability that compounds, developing people who develop others, creating systems that outlast any individual.

The most powerful signal a leader can send is genuine investment in something that won’t pay off until long after it would be easier to leave.

The compounding effect.

Engagement, like disengagement, compounds.

A seller who is genuinely engaged with a customer’s problem understands things the competition doesn’t. That understanding produces insights. Insights build trust. Trust changes the relationship. The customer feels the difference between someone executing a sequence and someone genuinely invested in their outcome.

That seller wins more. Winning builds confidence. Confidence enables deeper engagement. The cycle accelerates.

Disengagement compounds too. The seller going through motions qualifies loosely because they need volume. They don’t invest deeply because why go deep on something that probably won’t close. They discount late because winning something feels better than losing everything. Each behavior reinforces the next. Performance erodes.

This compounding works at every level. The engaged manager develops sellers who think better, who qualify better, who win more, who engage more deeply. The disengaged manager runs pipeline interrogations that produce sellers who hide, who game the system, who go through motions, who disengage further.

And it works at the organizational level. The company, known for genuine engagement with customers, attracts better customers, better talent, and better partners. The company, known for going through the motions, attracts people who are comfortable going through the motions.

The direction of the spiral, up or down, is determined by the daily choices of individuals. Starting with each of us.

The choice.

Mitch asked, “How do we light that fire?” I’ve been thinking about this, and I think the answer is both simpler and harder than either of us wanted.

The fire doesn’t need lighting. It needs permission.

Most of us started our careers with genuine engagement. We cared about the work, the customers, the craft of what we do. That didn’t disappear. It got buried, under metrics that reward the wrong things, under fear of standing out, under the rational calculation that going through motions is safer than going deep.

But buried isn’t extinguished. I’ve seen people who looked completely checked out come alive when someone finally asked them a question that engaged their mind. When someone trusted them enough to give them a real challenge. When they saw a leader who was genuinely invested in building something rather than managing their own career.

The engagement is there. In most people, at most levels, it’s waiting.

But no one is going to give you permission. Not your manager, not your CRO, not your board. The choice to be genuinely engaged is yours. It always was.

The question isn’t “how do we get people to care?” That question lets everyone off the hook, including the person asking it.

The question is: do I care? Am I engaged? Am I bringing genuine depth and investment to what I’m doing today, not because the system rewards it, but because it’s the kind of professional I want to be?

If the answer is yes, then act like it. Go deeper in the next conversation. Push back on the bad deal. Ask the harder question. Coach someone. Prepare like the outcome matters.

If the answer is no, if you’ve decided that this work, this organization, this role isn’t worthy of your genuine engagement, then be honest about that too. Maybe it’s time for a different kind of change.

Good enough isn’t just a race to mediocrity. It’s what happens when people who are capable of excellence stop asking themselves whether they’re truly engaged.  Whether they really care about what they are doing.

Ask yourself. Today. And answer honestly.

Afterword: my friend Mitch Little has practiced this through his distinguished career.  He’s written about this, far more deeply in his book CUSP, Leading by Serving When Outcomes Matter The Most.  As is typical of Mitch, he has made this available to everyone at no charge.  Be sure to download it, absorb and practice it.

Afterword:  Here is a great AI generated conversation of this post.  Enjoy!