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What former bosses, founders, and peers say executives need to be successful.
There is no shortage of advice about leadership: how to build a high-performing team, lead through change, manage a board, communicate, influence, and become a better CEO.
A founder hires a VP of Sales who has built the function three times before. A CEO brings in a seasoned CMO, CTO, or Head of Product precisely because this person knows things the company does not.
Quite often, and by design, the executive knows considerably more about their function than the person leading them.
That changes the relationship.
How much direction is useful? How much context is enough? When does support become interference? How do you give feedback to someone with 20 years of experience in a discipline you have never led yourself?
We realized we had an unusual place to look for these answers.
For years, near the end of our executive searches, Artemis has asked former bosses, founders, and executive peers - often people with serious operating credentials of their own - one simple question: “What advice would you give this person’s next employer to set them up for success?”
We love this question. The answers are specific, concrete and actionable.
After years of hearing variations on the same advice, we went through the archives, like detectives, to see if there was a pattern.
There was.
We analyzed 191 unique, completed reference conversations for senior-leader searches spanning 2019 through 2026.
The clearest finding was autonomy.
The language varied, but the idea was consistent: give them space, let them run, trust their judgment, and do not prescribe every step.
It makes sense. Companies rarely hire an experienced executive because they need another pair of hands. They hire them because they need judgment they do not currently have.
This is also where the relationship can get weird.
For years, a founder may have been the functional leader by necessity: CEO, salesperson, product lead, recruiter, and keeper of every piece of institutional memory. Then the company hires someone senior to own a meaningful part of it.
The founder may understand intellectually that the job has changed while still behaving like the functional owner.
But the data did not suggest executives simply want to be left alone.
Of the 102 references that recommended autonomy, only 18 described autonomy as the whole answer.
82% paired it with something else: context, clear goals, resources, feedback, strong counterparts, access to information, or organizational support.
The advice was less leave them alone and more: Set the conditions, then trust them.
The second-largest theme was clarity.
That is really the centre of the story.
Your CMO may know considerably more about marketing than you do. What they do not know is everything sitting inside your head: Why the obvious strategy was tried two years ago and failed. Which customer relationship is shakier than it appears. What the board is nervous about. What promise was made during the last financing. Which old decision is still shaping how a team behaves.
You may have accumulated that context over five years. Your new executive has been there five weeks.
One reference described a leader who would pursue whatever goal was put in front of them with enormous intensity. Their advice to the next employer was essentially: be thoughtful about the goal.
It is a good problem to have, and it illustrates why autonomy and context belong together.
A senior executive usually does not need you to know more about their function than they do.
You do not need to be a better marketer than your CMO to tell them customers are confused, or a better engineer than your CTO to say nobody understands the trade-offs being made.
You do not have to out-expert your experts. You do have to give them information they cannot get anywhere else.
Companies sometimes overcorrect once they hire someone genuinely senior.
The thinking becomes: Great. They own the function. One less thing to manage.
Not quite.
Senior people still need management. They simply tend to need a different kind.
They may not need help making a decision, but they may need their leader to back them once they’ve made it. They may not need another meeting, but they may need one piece of information everyone assumed they already knew.
The best environments described in the references were neither high-control nor completely hands-off.
They were closer to high autonomy, high support, and low interference.
One reference told the next employer to treat the executive as a true counterpart: establish clear lanes, trust their expertise, and build enough of a relationship that either person can ask the other for help.
Another essentially said it would be a waste to use the person only for the function they had been hired to lead.
That idea stuck with us.
Experienced executives accumulate pattern recognition well beyond their job descriptions.
A CFO has seen go-to-market problems show up in the numbers. A CTO has watched organizational structures fail. A CMO may have excellent product judgment. A People leader has probably watched more leadership teams implode than anyone else at the table.
You do not need everyone involved in everything. There is a special kind of misery reserved for organizations that operate that way.
But if you hired someone because their judgment is unusually valuable, you should probably create opportunities to hear it.
Tell them when they are off track, when the goal changes, or when something is not working.
Several references described people who could adjust very quickly once they had useful information.
That creates a fairly avoidable failure mode: leaders withholding feedback from exactly the people most capable of doing something with it.
Seniority can make this oddly uncomfortable. If the executive knows more about the function than you do, it can be easy to assume you are not qualified to challenge them.
That is not really the point.
The CEO has information the executive cannot have. They know how this person is landing with the board, what peers are struggling with, where confidence is slipping, and what has changed elsewhere in the company.
Only 6% of references explicitly raised prioritization, workload, or overextension, but the pattern was instantly recognizable.
Some high performers take on too much, say yes too often, go too deep, or see five important problems and start solving all five.
These are not usually motivation problems.
They are often the downside of the same characteristic that made the person compelling in the first place.
The edge and the strength are often the same characteristic under different conditions - the “shadow side,” as I like to call it.
The goal is not to sand every edge off. That is one way companies accidentally turn exceptional people into average executives.
Sometimes leadership’s job is simply to protect someone’s attention from their own ambition.
Early-stage companies spend enormous energy creating urgency.
The same dynamic showed up in the 14% of references that talked about challenge, growth, or meaningful scope.
Several described people who came alive around difficult, consequential problems and lost energy when the work became mostly incremental.
Companies often hire these people because of the steep trajectory that made them interesting in the first place.
They built something. Fixed something. Entered a new market. Inherited a mess. Took on far more than their title suggested.
Then they arrive in a senior role and spend three years maintaining something they once had the thrill of building.
Ironically, when we talk to senior leaders who are open to making a change, this is one of the most common reasons we hear - and often the first. Not that the company is terrible, or the boss is terrible, or even that they are particularly unhappy. The work has simply stopped stretching them.
When someone eventually leaves because they “wanted a new challenge,” the resignation may simply be the lagging indicator.
They do. Candidates generally do not hand recruiters a list titled People Most Likely to Destroy My Career.
Selection bias is real. But that criticism assumes the purpose of a reference check is to catch someone saying something bad.
It is not.
By the time we get to references, we have usually spent a considerable amount of time with the person already. We have heard how they describe their strengths, where they have struggled, how they work, what they have learned, and what they need around them to be successful. Along the way, we have formed our own hypotheses, questions, and curiosities.
References let us look at that same person from another angle.
We are not starting from zero. We are asking: does what we heard throughout the interview process hold up through the eyes of people who have actually worked beside them? Do the same strengths show up? The same edges? Does something we were curious about become clearer?
That is why a good reference check is less about finding a contradiction and more about finding pattern consistency.
“This person is amazing” is nice to hear, but it tells us very little.
A former boss saying the person tends to take on too much is more useful.
A peer independently describing them as the person who volunteers for every difficult problem is more useful still.
If another person then mentions that they sometimes need to be reminded to delegate, a pattern starts to emerge.
Maybe the candidate already told us some version of that themselves. Maybe we noticed it during the interview process. Maybe it resolves something we had not quite been able to put our finger on.
That is the useful part.
The best references are often not delivering a verdict at all. They are compressing years of experience working beside someone into a few practical observations about how that person operates, what brings out their best, and where they may need support.
For whoever is about to lead them next, that can be far more valuable than another thumbs-up.
Across 191 conversations, the advice was remarkably consistent:
Almost nobody told us the answer was more control.
You hired them because they bring judgment, experience, and answers you do not already have. Your job is not to replicate that expertise or stay at the centre of every decision.
It is to make success clear, give them the context they cannot get anywhere else, tell them the truth when it matters, and create enough trust for their judgment to actually matter.
That is how you lead a leader.
This analysis draws on Artemis Canada’s internal reference-check archive from 2019 through 2026.
Our recruiting database was built to recruit people, not conduct academic research. Unfortunately, some of us are PhD dropouts and ex-researchers, so we cannot resist.
We identified 191 unique, completed reference conversations for senior-leader searches spanning Director, Head, VP, and C-suite mandates for technology companies across North America. We excluded templates, incomplete records, non-senior searches, and duplicate versions of the same conversation.
Responses could fall into more than one theme, so percentages do not sum to 100%.
Reference conversations are confidential; examples have been paraphrased and de-identified.
Read more insights from our team.
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Founded by Kristina McDougall in 2013, Artemis has grown to become Canada’s most trusted boutique executive search firm for startups.
We recognize that our work takes place on the traditional lands of the Attawandaron, Anishinaabeg, Haudenosaunee, and Mississaugas of the Credit. We honour Indigenous stewardship and commit to embedding reconciliation into our work, holding ourselves and our clients accountable.
