Probation at Senior Level: Why Executives Fail in the First Six Months
Senior hires fail early more often than people admit.
The search took months. The board was confident. The new CFO or general manager arrived with a strong record and a clear mandate. Then, somewhere between month three and month six, it starts to go wrong. Trust slips. The CEO goes quiet. By the end of probation, everyone is wondering what happened.
It is rarely about skill. Most senior leaders who struggle early are highly capable. They struggle because of how they start: too fast, too slow, with the wrong people or on the wrong problems.
The good news is that most of it is avoidable. A few deliberate choices in the first six months make a big difference.
A note on probation itself. Many senior contracts include a probation or trial period, and the rules around these differ between Australia and New Zealand. Check what your contract says and get advice from an employment lawyer if anything is unclear. This article focuses on the practical side, not the legal one.
It covers why senior hires fail early, a first six months plan, early wins versus early changes, relationships to build first, signs it is going wrong and what to do if it is.
Why senior hires fail early
The patterns are familiar.
Moving too fast. Changing structures, systems or people before understanding why things are the way they are. It signals that you think the past was wrong, and the people who built it notice.
Moving too slowly. Spending months listening without making any decisions. The CEO starts to wonder what they are paying for.
Misreading the mandate. You thought you were hired to transform. The CEO wanted stability. Or the other way around.
Bringing the last job with you. Running the playbook from your previous company without checking it fits this one.
Neglecting key relationships. Spending time with the team but not the chair. Or with the CEO but not your peers.
Culture clash. A different pace, style or way of disagreeing that you do not adjust to.
Hidden problems. A finance team weaker than you were told, or numbers that do not hold up. How you raise it matters more than the problem itself.
Most of these come down to one thing: not taking the time early to understand the business, the people and what success really looks like.
A first six months plan
A simple plan helps you pace yourself. Treat it as a guide, not a script.
Month one: listen and learn.
Meet every key stakeholder one to one.
Confirm with the CEO what success looks like at six and twelve months.
Read board papers, strategy documents and the last two years of results.
Spend time with your team, both as a group and individually.
Months two and three: test and decide.
Share your early observations with the CEO privately.
Agree two or three priorities in writing.
Deliver one or two early wins (see below).
Start shaping your view on structure and capability.
Months four to six: act and build.
Begin the larger changes you have agreed.
Make any people decisions with care and support from HR.
Present your plan to the board, if appropriate.
Ask the CEO for honest feedback on how you are going.
For more detail on early planning, see the first 90 days in a senior role.
Early wins vs early changes
These are not the same thing, and confusing them causes many early failures.
Early wins are small, visible improvements that build trust. They solve a real problem people care about, without threatening anyone. Examples:
Fixing a monthly report the CEO finds hard to read.
Speeding up approval of a delayed supplier payment run.
Clearing a backlog of audit findings.
Giving the sales team a simple margin view they have asked for.
Early changes are structural. A new operating model, a system change or a team restructure. They may be needed, but they carry risk. Done too soon, they look like you are judging the past before you understand it.
A good rule: win trust with early wins first, then use that trust to make larger changes.
Relationships to build first
In the first six months, a handful of relationships matter more than any task.
The CEO. Agree how you will work together. How often you meet, how they like to receive information and what they want to hear about first.
The board chair and audit committee chair (for CFOs). Meet each early. Ask what they want from you.
Your peers on the executive team. They will decide much of your reputation. Ask each what they need from finance and what has been frustrating.
Your direct reports. Learn their strengths, worries and ambitions. Do not make quick judgements.
Key external parties. Auditors, bankers and major customers or suppliers, depending on the role.
Ask every person the same three questions: What is working? What is not? What would you do in my position?
How search consultants see it
When I worked in executive search, I always checked in with candidates and clients during the first six months. It was one of the most useful parts of the work, because it showed me what really made senior hires succeed.
The leaders who settled well had a few things in common. They were curious about the business before they had answers. They built strong relationships with the CEO and their peers early. And they checked in regularly on whether they were meeting expectations, instead of waiting for a formal review.
The ones who struggled often had the right skills but misjudged the pace. Some charged ahead. Others waited too long. Very few failed because they could not do the job.
Signs it is going wrong
Early signs are often subtle. Watch for:
Fewer one-to-ones with the CEO, or meetings that are shorter and more formal.
Being left out of decisions you would expect to be part of.
Peers going around you to your team or to the CEO.
Feedback through others, such as HR or a board member, instead of directly.
Your priorities shifting without discussion.
A sense of unease in your gut that you cannot quite name.
One sign on its own may mean nothing. Several together are worth acting on.
What to do if it is
Do not wait for the end of probation. Act early.
Ask for a direct conversation with the CEO. “I would value your honest view on how I am going so far. What is working and what would you like me to do differently?”
Listen without defending. Take notes. Ask follow-up questions.
Agree on two or three specific changes, and check back within a month.
Look at your relationships. Is there a peer you have neglected or a board member you have not met?
Get outside support. An executive coach or a trusted mentor can help you see what you are missing.
If it is clear the role is not right, think carefully about your next step. A calm, early conversation is usually better for everyone than a difficult exit later. See the first-time CFO for the specific challenges of stepping up for the first time.
Probation works both ways
Probation is not only the employer’s chance to assess you. It is also your chance to assess them.
Use the first six months to test what you were told during the search. Is the mandate real? Does the CEO back you when it counts? Are the numbers sound? Is the board engaged?
If the answers are mostly yes, commit fully. If several are no, raise them early and calmly, while there is still goodwill on both sides.
A quick self-check
Do you know exactly what success looks like at six months?
Have you met every key stakeholder one to one?
Have you delivered at least one early win?
When did you last ask the CEO for direct feedback?
Your next step
Write down your top three priorities for the next three months, then check them with your CEO this week.
If you want help positioning yourself for a senior role you can succeed in, my executive positioning work helps senior leaders get clear on the roles that suit them and start strongly.
If you are new in a senior role and want an outside view, book a complimentary Clarity Session.
