You’re mentoring someone towards promotion and are unsure how honest to be
Encouragement without an honest assessment can leave someone less prepared for the decision ahead.
Someone you manage wants to step up, and you are the person they are asking. The difficulty is not finding the time or the right development activity. It is that you like them, you work with them, you will still be working with them afterwards, and a panel will form its own view of them whatever you say. Encouragement is easy and costs nothing. An accurate account of where they stand is harder, and it is the thing they most need from you.
Presenting symptoms
- Your encouragement has become general, and you notice you are praising effort rather than naming anything specific.
- The assessment you could support if you were asked today is not the one you have been giving them.
- A post has appeared, or will soon, and the conversation you have been postponing now has a date attached.
Possible causes
- You may not actually know whether they are ready, because nothing you have given them would show you.
- They may be pursuing a promotion because it is the visible next thing rather than because they want the work it contains.
- You may know they are not ready and have been waiting for them to reach that conclusion themselves.
- You may know they are ready, and part of you may not want to lose them.
You do not know, because you have never given them anything that would show you.
Your most useful next step: Give them a piece of work that carries real accountability rather than visibility, at the level where they decide and check with you before acting rather than at report-back, and then watch what happens without rescuing it. Move towards full ownership as the evidence supports it, rather than starting there while readiness is still unknown. Work with accountability attached provides evidence that conversations alone cannot, for them as well as for you. Choose something where the consequences of it going wrong are recoverable.
Lead behaviours
You are not sure they want what they say they want.
Your most useful next step: Before you tell them anything, ask what they think the role involves, what they would be doing differently in a week, and what they would miss about the job they have now. People pursue promotions because they are the visible next thing, and finding that out early is a service rather than a discouragement.
Lead behaviours
You know they are not ready, and you have been hoping they would work it out.
Your most useful next step: Say the specific thing, once, early enough for it to be useful rather than the week before a deadline. Name what it is, why you are saying it, and what would have to be different. Then agree with them what happens next rather than prescribing it, so that the plan is theirs and the judgement was yours.
Lead behaviours
You know they are ready, and part of you does not want to lose them.
Your most useful next step: Say it plainly, and say it early enough to be of use. Name the staffing interest to yourself first, because letting it shape the advice would compromise the very assessment they came to you for. The question in front of you is their career rather than your staffing, and those are two separate problems that you happen to hold at the same time.
Lead behaviours
Core behaviours
The book names the exact failure this record is about: the tendency to avoid difficult conversations for fear of creating conflict or upsetting a colleague. It is equally clear that accountability is not confrontation but an investment in someone’s development, and it offers the opening that makes the difference, which is saying why you are saying it. Nothing else in the framework holds both halves of that.
You need an accurate reading of where they stand rather than the reading that affection and proximity produce. The book’s point is that confronting the reality is the foundation of progress rather than an act of negativity, and here the reality includes evidence you may not have gathered because you did not want to find it.
The book defines this as understanding strengths, working styles and motivations, and is explicit that it is about recognising how people work best rather than cataloguing what they can do. Two things depend on it here: whether what they want is the role or the status, and how this particular person will be able to hear an honest answer without shutting down.
The book’s instruction is to stay curious longer and to reach for advice more slowly, moving from directives to a coaching stance that understands before solving. A mentor who delivers a verdict before finding out what the person actually wants has answered a question nobody asked, and will frequently find they were wrong about the question.
The book states directly that delegation is part of succession planning and that stretch assignments slightly beyond someone’s current skill set build readiness, and its five levels give you the instrument. Its Delegation Readiness Matrix also settles where to start: full autonomy is the book’s response to competence already established, not the means of discovering it. Begin where they decide and check before acting, which carries real accountability while the evidence is still being gathered, and move up as it is earned. This is how the mentor stops guessing. Delegation here generates the evidence; it is not, as in 2.7, the mechanism for distributing authority across a team.
Secondary behaviours
Use this after the honest conversation rather than instead of it. The book gives this its own example: working with a colleague on something aligned to an area they have expressed future aspirations about. The judgement about readiness is yours to make and state; what happens next is better shaped with them, and a plan they helped build is the one they will actually follow.
Use this on your own position. The book’s formulation is that the most humble leaders hold the highest aspirations, not for themselves but for their colleagues, and that they build capacity rather than empires. A mentor has an interest in keeping a strong colleague, and naming that interest to yourself is what stops it quietly shaping the advice.
Use this where the answer is not this year. One of the book’s own examples of the long game is the investment in a young teacher who becomes an exceptional head of department. A mentor whose honest answer is not yet is making that investment rather than withholding support, and saying so is what stops it being heard as a refusal.
A useful first action
Write down the honest assessment you can currently support, including anything you do not yet know. Then identify the sentence you would be most reluctant to say. If the assessment is incomplete, that tells you what evidence has to be gathered before the conversation. If it is complete, that sentence is the conversation.
Suggested approach
- Write down the assessment you can currently support, including what you do not yet know, and find the sentence you would be most reluctant to say.
- Find out what they actually want and what they believe the role involves, before you tell them anything.
- Where you do not know how ready they are, give them work that carries real accountability, starting where they decide and check with you before acting, and watch what happens.
- Say the specific thing, once, early enough to be useful, and say why you are saying it.
- Agree with them what happens next, rather than handing them a plan.
- Make sure your assessment is one they have actually heard, so that nothing about where you think they stand arrives later as a surprise.