The first 90 days of a senior hire: define success first

When a senior leader joins, the first quarter is when they learn the business and start taking decisions off someone else's desk. How far they get depends partly on them. It also depends on whether the person who hired them has said, in writing, what the role should look like once it is properly theirs.

Without that, the new leader works from guesses. They may wait to be told what matters, or push hard on the wrong things. The CEO, meanwhile, judges progress against a picture that exists only in their own head. Both end up frustrated, and neither has done anything unreasonable.

This post covers what to write down before the first day, how to hand the role over in stages, when to make it fully theirs and how to stay close without taking the work back. It draws on how I described hiring and handing over roles in my own service companies, in podcast episodes from 2020 and 2022 and an interview in 2025. The stages below adapt those lessons to an experienced senior hire.

DisclosureJake Jorgovan co-founded Alpha Apex Group, which this essay links to.

Write down what success looks like at day 90

In a 2020 episode on hiring, I described a document I liked to put together for a new hire. It answered the question "what is success at 90 days?" by listing what the person needed to have achieved by then to have grown into the role and to be owning it. I suggested writing it before the hire if possible, and during onboarding at the latest.

In my example, by day 90 the person would completely own the operations for one segment of the business: part of the process, communicating with the team and knowing everybody. They would be working with the operations director and the sales team, and would have documented their day-to-day in a playbook. The CEO, I said, needs to define those criteria so the person knows how to succeed. Without them, a new hire ends up waiting to be told what to do, which is delegation, not ownership.

For a senior hire, make ownership the core of the day-90 list. Don't expect a new chief revenue officer to have rebuilt the sales organization by then; a list that expects it makes a reasonable first quarter look like a failure. What you can expect by day 90 is narrower and easier to check. In a hypothetical case, the new CRO runs the weekly forecast review, has met the largest accounts, has agreed next year's hiring plan with finance and has written down how the team qualifies a deal. Put longer-term commercial targets in a separate plan with their own timeline, and include any commercial commitments due in the first quarter alongside the ownership criteria.

Above the list, put one sentence. In a 2022 episode on leading others, I recommended defining success for each role in a single sentence and repeating it until it became a filter for everything the person did. For our podcast managers, success meant every episode published on time and without errors. For an enterprise client strategist we had recently hired, it meant our enterprise clients achieving their business objectives. A senior hire needs the same thing for the whole function: the one result the role exists to produce.

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The approach described in this article, shown as a visual guide.

If you can't write it, learn the function first

Sometimes the document is hard to write because the person hiring does not understand the function well enough to say what good looks like. In a 2025 interview with Alex McClafferty (opens in a new tab), I put it this way: "there's some level of competency you need in all aspects of the business to be able to hire someone effectively."

I had learned that the hard way. I went through several painful finance hires before I took finance courses and learned the subject myself, which made me much more effective with a fractional CFO. Operations was similar: once I understood what the company needed from its systems, my next COO or operations hire was excellent, because I knew what I was looking for. When you are weak in an area, I said, a good tactic is to learn as much as you can and find an adviser or a coach.

In a larger company the CEO won't do the job themselves, but they need enough grasp of it to write the day-90 list and to judge whether it has been met. If that grasp is missing, close the gap before the search, with an adviser, a board member who has run the function or a search partner who can explain what the role involves.

Hand the role over in stages

The same 2020 episode described the plan that goes with the 90-day document, because you can't put the whole role on someone's plate on day one. I set out four phases. The new person shadows someone and learns the processes. Then they do the work while their manager watches. Next they work without being shadowed, sending questions and checking in about once a week. Finally they simply report the metrics and updates each week. The phases vary from role to role.

An experienced executive does not need to be shown how to do their job. They do need to learn how your business works before they change it. For a senior hire, the four phases translate like this.

1. 1

   Learn the business

   The new leader meets the team, their peers and the main customers, and sits in on the meetings and decisions they will soon own. Whoever holds the role now, the CEO or an interim leader, keeps running it.

2. 2

   Run it together

   The new leader starts making the decisions, with the current owner in the room or reviewing them. Differences of judgment come out here, while they are still easy to discuss.

3. 3

   Own it, with weekly check-ins

   The decisions are theirs. They bring questions, and you meet each week to go through them.

4. 4

   Report on the agreed measures

   They run the function and report progress against the day-90 list and the longer plan. Your part is to review, ask questions and help with the obstacles they raise.

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The approach described in this article, shown as a visual guide.

How long each stage lasts depends on the role and on what the leader already knows. Both of you should know which stage you are in, and what moves you to the next.

Set the date the role becomes theirs

Moving from running it together to owning it needs a decision. The advice I passed on in 2022 from my adviser, Anthony Tombolio, was blunt: "you got to set the date and rip the bandaid." Pick the day after which the person is responsible. They can still come to you with questions, and you can keep regular one-on-ones, but from that date the role is theirs.

I described doing this with my guest scheduling team. After a couple of months of shadowing came the uncomfortable question of whether they were really ready to take it over. I set a date. We kept weekly check-ins and metrics to measure against, and from then on they were responsible for solving the problems.

The thing to avoid is hopping back in to do a little of the work whenever the new owner does not seem ready. It is a dangerous cycle: it damages the person's confidence, and it means you are still not letting go.

That episode had small companies in mind, where, as I said then, promoting a strong doer into management was the usual path and hiring a manager from outside was less common. With an external senior hire, the date does one more job: it tells the rest of the organization where decisions now go. Announce it, and send the questions that still arrive on your desk to the new leader.

Stay involved without taking the work back

Setting the date does not mean disappearing. When a problem comes up, ask what they would recommend instead of solving it. Sometimes the answer is close to what you would have said, and telling them so builds their confidence. If it isn't, it becomes a coaching moment. In 2022 I was holding one-on-ones with the people I was developing into leadership roles: weekly for the most senior, monthly for those further removed.

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In Pew’s February 2023 survey, workers receiving frequent feedback were more satisfied with the amount they received. The sample excludes self-employed workers. This association does not establish that more feedback caused the higher satisfaction.pewresearch.org (opens in a new tab)

Letting go did not come easily to me. Talking to Alex in 2025, I said I had found it hard to trust people fully and would manage far too closely. What helped was giving people a clear outcome, defining what success was, asking what support they needed and asking them to check in. I also said some of my partners had the opposite problem: they delegated too readily and only later asked what was going on. Even so, I said that if you hire the right people, trusting them is almost a better model for quicker growth than being overly controlling, though each approach has its pros and cons. In a senior hire's first quarter, the written criteria and a regular check-in let you extend that trust and still see how the work is going.

There is a good reason to resist stepping back in. I held on to account management for years, as I told Alex in the same conversation. When I brought in an account manager who had come from Salesforce and was trained in the work, the upsells came immediately. I had only been avoiding churn. A senior hire who owns the role may do it better than you did.

If the new leader is struggling at day 60, start with the document. Back in 2020 I cited one of my favorite lines from The One Minute Manager: whenever there is a problem with a team member, look at the manager. What we want from a new hire often exists only in our heads. Check that the day-90 list actually said it, then decide what needs to change.

If your new leader started on Monday, could you hand them this page with every line filled in? If not, that is the work to do before they arrive.