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In This Left-Hand Column:
“Did I actually say what I went in to say, or did I soften and hedge so much that a bloodhound couldn’t find my point? I’m probably going to lie awake in bed dissecting what every subtle eye twitch implied.”
– Internal monologue after a high-stakes meeting
Step into this scene for a moment:
You’re walking out of a hard conversation with your CEO. Not a status update or quick question, but something challenging. The kind of exchange you spend days dreading, searching for an “out.”
As you leave, how do you think it went?
If the answer is: “Pretty good. I said what I needed to say, I left with clarity, and I trust my read of the exchange.” Then, congratulations! You can sit this issue out. Forward it to a colleague who may need it more, and I'll see you next month.
Otherwise, pull up a chair.
Do You Get Along With Your Boss?
This is where many executives get tripped up. We tend to boil the health of our working relationships down to: “Do we get along?”
But a more impactful question is this:
Is how we get along effective? For us? For the organization?
Too cozy, and you stop pushing each other. Too adversarial, and you stop getting the best out of each other. The ideal balance is built on these pillars:
Mutual knowing: Beyond surface-level facts about each other, do you have shared context? Are you aiming for the same North Star? Are you operating from the same (or complementary) values?
Trust: Are you able to extend each other more latitude, more benefit of the doubt, more curiosity? Do you trust their judgment when you don't have the full picture, and do they trust yours? Access, in and of itself, doesn't generate trust; it takes multiple moments when something is at stake.
Resilience: What is the capacity of your relationship to weather difficulty? Is there room to address mistakes, trade feedback, and set clear expectations? A viable relationship can absorb friction, name it, and recover. Mere contact tends to sweep any friction under the rug, so the uncomfortable thing never gets addressed. Until a high-stakes moment forces it, and there's no relational cushion to hold it.
You can build functional versions of all three pillars through professional discipline alone. If all you have with your CEO is shared context, clear communication, and operational alignment, that’s a perfectly workable dynamic.
But it’s more of a floor than a ceiling.
The informal dimension, the personal connection, the sense that you actually know each other as people, acts as a kind of lubricant for everything else. Connectedness is the difference between a good working relationship and one that amplifies your impact.
How Do You Measure It?
There's no universal diagnostic for the quality of your relationship with your CEO. What "healthy" looks like for you will differ from what it looks like for the exec team across town.
But it still helps to have a way of locating yourself: something casual enough to avoid “I dunno” as the default answer, but utilitarian enough to be worthwhile. Ideally, your gauge should encourage you to view the relationship as an average over time rather than as a single snapshot.
Here's a scale you can use as a starting point:
Relationship State | What It Feels Like | The Cost/Benefit |
|---|---|---|
Friction | Small static accumulates around every interaction. You brace for meetings. Disagreements feel deeply personal even when they aren't. | The relationship is tenuous, constantly draining energy you can't easily get back. |
Neutral | The work gets done. Communication happens. There's no overt tension, but no real warmth, depth, or strategic curiosity either. | You'd describe the dynamic as "fine," and you wouldn't be lying, but you're leaving a lot unsaid. |
Flow | You move together easily. You can disagree, push back, share half-formed thoughts, and recover quickly from missteps. | Your impact and influence get a shot of rocket fuel. (More on this in the next section) |
Recognizing where you live on the scale is a significant win. (Even if where you currently are leaves a ton of room for improvement.) Because the CEO relationship that's underperforming often feels fine. Functional.
Right up until the moment it isn’t.
“Fine” Is Good Enough, Right?
I spent years assuming that being good at my job was enough and that my work would speak for itself. Moreover, the idea of intentionally cultivating a personal relationship with my boss felt awkward and performative. The hallway chit-chat, the after-work hang; it all seemed unnecessary if my results were good.
What I understand better now is that organizations run on trusted, visible, well-connected people who produce results. Execution and competence matter, and nothing in this issue substitutes for them. But at the executive level, executing well is increasingly inseparable from your working relationships. And none of those relationships matters more than the one with your CEO.
Your CEO controls your mandate, your resources, and the political capital that moves your agenda. So when that relationship is purely functional, you get to do your work. But when you move your relationship toward flow, you multiply your impact:
You get the benefit of the doubt when something goes sideways. Instead of evaluating what they see at face value, they extend trust and curiosity into the gap: I know this person. There's probably more to the story. That latitude doesn't exist in a purely functional relationship.
You get early signal instead of late surprises. CEOs who feel genuinely connected to you are more likely to share half-formed thinking, shifting priorities, and concerns they haven't fully articulated. In a functional-only relationship, you hear about changes once they're decided. In a stronger one, you're in the conversation before the decision is made.
Your influence expands. The CEO delegates more consequential work to you because they trust you as a proxy. Decisions move faster because you don't need to bottleneck everything through a check-in. The CEO starts to experience you as an extension of their leadership rather than a direct report who needs managing. That's a fundamentally different position of power to be in.
So what's at stake isn't first place in a popularity contest. It's whether you are operating at your maximum potential, and thereby helping the company reach its maximum potential. At a certain level of leadership, what determines if you reach that potential isn’t the quality of your work, but the quality of your relationships.
Only you can answer whether "fine" is good enough. As you decide, consider what you're leaving on the table.
Note: What follows assumes you're somewhere around neutral on the scale above. If you're all the way at the friction end with a smattering of toxic for good measure, that's a different conversation, and it may be time to look for the nearest exit.
Shift From Default to Design
Lest you think I’m arguing that you start sending your CEO roses and Valentine’s Day cards, I’m instead advocating for more intentionality in your interactions.
Here’s what makes up the foundation of an intentionally designed CEO relationship:
1. Formal operating cadence. OKRs, exec team meetings, structured 1:1s tied to the business. This includes being explicit about decision rights and boundaries: when is it the CEO's call, and when is it yours? Ambiguity here is one of the most common sources of executive-level tension, and one of the easiest to resolve with a single conversation.
2. The feedback loop. How are we actually doing? How is the flow of our work? Is there tension that hasn't been named? Is there something I'm missing about what you need from me right now? When clients come to me describing a CEO relationship that feels "off," it's almost always because an intentional feedback loop doesn't exist.
3. Reactive communication. The Slacks, the urgent texts, the what-do-we-do-about-this pings. Most executives have this one in abundance. It tends to become the default mode of the relationship, and everything above (the elements that matter most for the relationship's health) gets crowded out.
These three elements are the vegetables of the CEO relationship; they tend to fall in the “yeah, I know. I should be doing that” category. They're not glamorous, but their impact is reliable.
Then there’s the “multiplier” ingredient that makes the relationship thrive:
4. Connectedness. Ever found yourself in a conversation with someone you just met and lost track of time? That feeling of just vibing with someone, human-to-human, is what I mean by connectedness. It's what gives you both, as CEO and exec, the space to interact more candidly.
This is a two-way street in theory, but in practice, it typically falls on the exec to initiate. Founder-CEOs are intentional about almost everything that keeps the company alive (fundraising, product, board management, etc).
What they tend to leave to chance is nurturing rapport with their leadership team, betting that it'll develop organically through proximity and shared stakes.
So, the intentional approach is yours: Find what makes your CEO most human and meet them there. A genuine shared interest or earnest curiosity; a context where the title recedes a little.
For one client, it was Friday-night video games. For another, an informal monthly meal. Neither had an agenda, but both became spaces where what was really keeping their CEO up at night could surface. The point isn't the format, but it's the intention behind it.
“Either you vibe with your CEO, or you don't,” the thinking goes. And if you don't, you stay focused on the work and call it a day. Right? Oftentimes, that's giving up more agency than we realize we have.
When You Just Can’t Relate
Developing a personal connection can sometimes feel like trying to weave a cozy blanket out of thin air: there’s just nothing to work with.
I worked at a company where the leadership team was obsessed with cricket. The first 15 minutes of every team meeting would end up being animated banter about this match or the other. I'd sit there blank-faced, waiting for the conversation to shift to something I could participate in. And even earlier in my career, my boss and a colleague spent chunks of downtime comparing luxury watches. I remember thinking they were nuts: $10 grand for something that tells time the same way my Target clearance watch did?! I also remember sitting there silently.
In both cases, nobody was trying to exclude me. They were just being themselves, talking about what they cared about. And I had more choice in those moments than I exercised. Not to transform myself into a cricket fan or a watch collector, but to get curious: “$10,000?! That's wild. What makes a watch worth that to you?"
All humans have something in common, even the ones who seem the most different from you. The question is whether you're willing to go looking for it. This looks like: paying attention, remembering things, and showing up where they are. One CPO I know started reading her CEO’s favorite books, and it made a significant difference in understanding them and their perspectives.
However you choose to, pick a path that goes a fraction deeper than “How was your weekend?”
And if, after genuinely trying, the other person doesn't reciprocate, that tells you something useful too: you've found the boundary of what's possible, and you can make your choices from there rather than from avoidance.
But Jess… Isn’t It Too Late?
It would be pretty convenient if you’re reading this issue just before entering a new role at a new company, so you get to approach your CEO-Exec relationship with a fresh canvas.
But, more likely, you’re years deep in a “fine, I guess” situation with your CEO, and suddenly taking a different approach would feel incredibly awkward.
The biggest barrier to resetting a CEO relationship is that neither party wants to name the problem. The executive waits for a signal; the CEO assumes things are fine or has already quietly decided. Someone has to go first, and in my experience, it almost always has to be the executive.
How you take that first step (and what follows) will look different for everyone. So rather than a script, think of the following as inspiration:
Start with the frame, not the feelings.
Don't say: "I feel like things have been off between us." That puts the CEO on the spot in a way that tends to create defensiveness rather than openness.
Do say: "I want to make sure I'm showing up in the way that's most useful to you and the organization right now. Can we spend 20 minutes on how we're working together, not just what we're working on?"
That reframes the conversation from interpersonal complaint to operational upgrade, which is the frame most CEOs can accept without raising their guard.
However it comes out, keep the setup brief. If you over-explain or over-apologize here, the CEO hears a complaint rather than a partner who's paying attention.
Rebuild shared context. CEO priorities shift fast at fast-changing companies, and it's entirely possible that you're operating on a picture that's out of date. What's keeping them up at night right now? What's changed about their board dynamics, their competitive landscape, or their own confidence in the company's direction? The misalignment you've been feeling may simply be because you're optimizing for a version of the company that no longer exists in the CEO's head.
Re-contract explicitly. Agree on how you'll work together going forward: how often you'll meet, what format those conversations will take, how you'll flag misalignment when it starts to build rather than after it's calcified, and what "proactive communication" actually means in practice between the two of you. The power of this step is that it converts a vague sense of "we should do better" into something concrete enough to hold each other to.
Radical ownership. This step kicks in when the gap is a trust fracture rather than a break or a drift. Acknowledge the specific incident. Own your role in it without conditions or counter-arguments, even if the situation was genuinely complicated and your version of it is more nuanced than theirs. Pair the acknowledgment with a concrete behavioral commitment, something visible that they can watch for. And then follow through consistently, because trust is rebuilt in small repeated actions.
The Choice to Opt Out
There's a point on the spectrum (and only you can locate it for your situation) where the question shifts from "How do I improve this relationship?" to "Is this still worth my investment?"
Some of you have been doing the math this whole time, weighing what intentional cultivation would actually require of you, and arriving at the conclusion that the cost is too high; that what I describe would shade into self-erasure, a betrayal of your values.
That is a valid call to make.
Nothing I've written here is a prescription. The main message of this issue isn't "you must cultivate this relationship intentionally." It's that you can.
“We get along fine” is what the leaders I work with say when they’ve accepted the default but would benefit from flexing their agency. That agency includes the choice to opt out: eyes open, willing to accept and absorb the impact that choice has on your work and your trajectory.
Whatever you choose in your relationship with your CEO, the value is in the choosing, and the harm is in letting it happen to you.
REFLECTION:
Where on the spectrum does your relationship live right now? And where would you say it lived three months ago? Six months ago?
Of the foundation elements (operating cadence, feedback loop, reactive communication) and the multiplier (personal connection), where are you strongest? Where is the gap widest?
What does the gap tell you about the relationship? Or about what you've been avoiding?
What’s one simple, concrete thing you can do to start closing that gap?
Keep reading, keep leading,
Jess
P.S. If The Left-Hand Column has resonated with you, consider supporting my work by clicking on one of the ads below. It's a small action that has a big impact!
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