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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.
A common mistake: hiring for their judgment, then overriding it.
We analyzed 191 unique, completed reference conversations for senior-leader searches spanning 2019 through 2026.
The most common requirement for a successful outcome, giving autonomy.
53% of references recommended giving the person trust, ownership, or meaningful room to operate.
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, skills, and experience 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 they have handed over the role, while still behaving like the functional owner.
Hire for judgment, then micromanage it, and you’ve paid a premium to neutralize it.
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, give them context, then trust them.
The second-largest theme was clarity.
38% of references explicitly talked about clear goals, expectations, business context, or a definition of success.
And across the full dataset, 73% mentioned either autonomy or 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.
Autonomy without context can look a lot like abandonment.
With scale, a great founder will hire functional leaders who are more knowledgable and skilled than they are. But the founder or CEO will always bring necessary context.
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.
But also, don't over-index on autonomy.
Companies sometimes overcorrect once they hire someone genuinely senior.
The thinking becomes: Great. They own the function. One less thing to manage.
Not quite.
30% of references talked about support, resources, coaching, or strong counterparts. Another 23% talked about inclusion and actually using the person’s judgment, while 20% emphasized direct communication and feedback.
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,and because they have seen the challenges you'll soon be facing, you should probably create opportunities to hear it.
The feedback finding was similarly straightforward: Be direct.
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.
For a highly coachable person, delayed feedback is latency.
Across 191 conversations, the advice was remarkably consistent:
Underneath all of that were five recurring ideas: autonomy, clarity, context, support, and candour.
Give senior leaders meaningful ownership. Make the destination clear. Share the important context that only you have. Give them the backing and resources to do the job. And be direct enough that they can adjust quickly when something changes.
There is also a bigger implication for founders.
As a company grows, the job of the founder has to grow with it. Early on, leadership often means being the person with the answers: selling the product, making the calls, knowing the customer, reviewing the work. Later, it increasingly means creating the conditions for other highly capable people to make great decisions without you at the centre of all of them.
That requires its own development as a leader. The skills that helped you build the company are not always the same skills required to lead the executives you hire to scale it. Delegating real authority, communicating context, giving candid feedback, and learning when not to intervene all become part of the job.
Clarity without control. Support without interference. Trust without absence.
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.