I've worked with eleven mid-market CEOs over the past twelve months — different industries, different scales, different problems. The engagements have ranged from one-off advisory weeks to multi-month strategy work. The variation is real, and yet seven patterns kept showing up in ways consistent enough that they're worth documenting.
Pattern 1: They're running the company from too high up
Almost every mid-market CEO I worked with this year was operating at a level of abstraction that wasn't serving them. They knew the strategy. They didn't know the unit economics in their own business well enough.
The shift that consistently helped: descend two levels. Not into operations — into the specific economics of how each line of business actually makes or loses money. The CEOs who do this regularly make better strategic decisions. The ones who don't are repeatedly surprised by what their own businesses are actually doing.
Pattern 2: They're hiring ahead of clarity rather than ahead of growth
"Hire ahead of growth" is conventional wisdom. The mid-market CEOs I see struggling are mostly hiring ahead of clarity — bringing on senior people before the role is well-defined, betting that the right hire will figure out the role themselves.
This works when the hire is exceptional. It often doesn't when the hire is good but not exceptional. The CEOs producing better outcomes have been more disciplined about clarifying the role first, then hiring against it. Slower. More accurate.
Pattern 3: They overestimate how much their team agrees with them
This was the most consistent surprise. CEOs would describe a strategic direction as if it were settled. I'd talk to the next layer down and find that several of the senior team were privately doubtful, had concerns they hadn't voiced, or were quietly working in different directions.
The cost is execution drag. The team isn't fully aligned but no one is having the necessary conversation. The CEOs who get this right tend to actively surface disagreement rather than wait for it to find them. The ones who don't are surprised when initiatives stall mid-execution.
Pattern 4: They're running too many strategic initiatives
The median mid-market CEO I worked with this year had between five and nine "strategic priorities." Most are doing one or two well. The rest are running on inertia.
The work that consistently helped: ruthless prioritisation. Three strategic priorities, maximum, with explicit decisions about what is being deferred. The deferrals are often the harder conversation than the priorities. The CEOs willing to have those conversations end up moving faster on what they did keep.
Pattern 5: They're measuring the wrong things
Most CEOs I worked with had monthly dashboards full of metrics. Most of those metrics weren't the ones that actually predicted business performance. The dashboards were optimised for ease of measurement rather than for predictive value.
The shift that helped most: identify the three to five metrics that, if they moved meaningfully, would change the trajectory of the business. Build the leadership cadence around those. Most other metrics are noise.
Pattern 6: They're spending too long on the wrong meetings
Every CEO I worked with this year described being too busy. When I looked at their calendars, the busy was usually optional. Recurring meetings that had outlived their usefulness. Standing reviews that should have been async updates. Customer meetings the COO could have run.
The CEOs who got their calendars under control reclaimed substantial weekly hours that they then deployed against the strategic work they'd been complaining they didn't have time for. The complaint was usually about calendar discipline rather than about the strategy itself.
Pattern 7: They're reluctant to fire executives who aren't working out
This is the hardest pattern, and the most consistent. Almost every mid-market CEO I worked with had at least one senior leader they privately knew wasn't working out and had been delaying action on for six to eighteen months.
The cost compounds. The wrong senior leader holds up hiring of better leaders, slows the team's development, drags down execution. The CEOs who eventually act on these decisions almost always say afterward that they should have acted six months earlier. The ones who keep delaying continue to pay the cost.
The underlying observation
What surprises me most across these patterns is that they're structural rather than situational. The same patterns appeared across very different companies — different industries, different scales, different specific problems. The implication is that mid-market CEO work has shape that the individual leaders are partly responding to and partly creating.
The CEOs producing the best outcomes weren't necessarily the smartest or most experienced. They were the ones who had built habits — descending into unit economics, surfacing disagreement, prioritising ruthlessly, measuring honestly, defending their calendars, making hard people decisions on time — that the harder-struggling CEOs hadn't.
The good news is these are habits, not traits. They can be built. The CEOs I've seen build them have done so deliberately, often after recognising the cost of not having them.
What I'm doing differently in engagements now
Based on this year's pattern, I've started doing three things more consistently in new engagements:
- Starting with a unit economics deep-dive in the first week, regardless of stated scope
- Running explicit "what are you not saying" sessions with the senior team within the first month
- Forcing prioritisation conversations early rather than letting them surface organically
Each of these surfaces the patterns above earlier in the engagement. That earlier surfacing tends to make the rest of the work more useful.
The harder question
What I haven't fully figured out is why the CEOs who recognise these patterns intellectually still struggle to act on them. The recognition isn't the bottleneck. The action is. I have working theories — fear of conflict, attachment to comfort patterns, the social cost of disrupting team dynamics — but none feel complete.
That's the work for next year's engagements. Pattern recognition is the easy part of consulting. Translating recognition into actual action by the leadership team is the harder part. Twelve months in, I'm better at the first than the second. Plenty of room to improve on both.
