Questions to help a client revisit direction

When you say the direction out loud now, what part of it still sounds like you?

Say it in one breath, then stop. The word you stumble on is usually the one to stay with.

• Say the direction the way you would tell a friend this week.
• Which word in that sentence would you change?
• If you kept only half of it, which half would you keep?

What part of this direction is still worth the effort it asks of you?

Name the piece you would defend, even if the rest of the plan feels shaky.

• Name the one part you would be sorry to drop.
• Which part are you still doing because you said you would?
• If the plan had to shrink, what would you tell me to protect?

Where has this direction started to sound like it belongs to someone else?

People stay loyal to a plan after they have outgrown it. This question makes room to say so.

• Whose voice do you hear when you describe the plan?
• What did you agree to early that you would word differently today?
• If nobody else had a vote, what would you change?

What would have to be true for this direction to still be right three months from now?

Name the conditions. You can change them later.

• What would you need to see happening by then?
• What would tell you it had stopped fitting?
• Who else would need to be willing to live with it?

What is different in your week now from when we started this work?

Start with the calendar. A concrete change is easier to trust than a mood.

• What takes more of your time than it did at the start?
• What have you stopped doing?
• What small change surprised you?

What have you tried since we began, and what did the try show you?

A conversation counts. So does finding out you hated the try.

• What did you actually do, even once?
• What did you learn that you could not have guessed beforehand?
• What are you unwilling to try again?

What outside this work has changed the picture?

A change at home, or a new offer, can move a plan. Say what arrived.

• What happened at home or at work that was not on the table when we started?
• Which change looks temporary, and which one looks like it will stay?
• What do you wish I had known about the last month?

If we were starting this work today, what would you tell me first?

You learn what matters by doing the work. This question asks for the update.

• What felt too early to say at the start?
• What do you understand now that you did not then?
• What should the next conversation begin with?

What have you noticed about yourself that caught you off guard?

Leave it open. The surprise can be something you liked, or a limit you found.

• What did you enjoy more than you expected?
• What wore you out in a way you did not predict?
• What did someone else notice before you did?

Which recent hour felt closest to the life you want more of?

One afternoon tells you more than a label would.

• Where were you, and what were you doing?
• Who else was there, if anyone?
• What about that hour do you want more of?

What have you been putting off, and what is that delay telling you?

A delay can be fear. It can also be a task that was never yours. You do not have to sort that out today.

• What have you postponed more than once?
• When you imagine doing it, what do you feel?
• Do you want help with it, or room to set it down?

What rule are you using on yourself that you would not use on a friend?

Get the private rule into the open. You can decide what to do with it later.

• Complete this sentence: I keep telling myself I should...
• Where did that rule come from?
• What would good enough look like for the next month?

If retirement is on the table, what from your working life do you still want in that chapter?

Look for what carries forward. Leaving a job and leaving a useful part of life are two different moves.

• What from your work do you want in the years after the job?
• What would feel wrong to keep doing once you are no longer employed?
• Who needs to hear that this chapter might mean stopping, rather than switching jobs?

If paid work took up less of the month, or none of it, what would you organize the month around?

Answer this if retirement or a smaller role is in view. If the full work week is staying, treat the answer as a boundary.

• What would a week be built around if the job no longer filled it?
• How much paid work, if any, do you still want in the picture?
• What would you miss if the job went away?

Whose picture of your retirement, or of your next job, are you still trying to live up to?

Someone else may be holding a picture of this chapter. Name whose it is.

• Who would be surprised if you changed course now?
• What have they said they want for you?
• What do you want them to understand that they do not yet?

What do you want this chapter to make possible that the last chapter did not?

Name a possibility. Time with a person, or a kind of day, is a complete answer.

• What did the last chapter make difficult?
• What do you want more room for?
• If this chapter went well, what would a friend notice about your life?

What do you want the next month of this work to be about?

A month is easier to be honest about than a long plan.

• Which question do you want us to stay with?
• What are you done talking about for now?
• What would a useful month look like at the end of it?

What conversation do you need to have next, and with whom?

The next move is often a talk with a specific person. Name them before you name a decision.

• Who has not heard the updated direction?
• What have you been saving to say?
• What answer are you uneasy about hearing?

What are you willing to try before we talk again?

Keep the try small enough for a full week. One try is enough.

• What could you do in a single hour?
• What would you learn from doing it?
• What do you want from me before you try?

What do you want to know, or have written down, before we stop today?

Use this near the end. It shows whether the time did what you came in for.

• What is still unclear?
• What decision, if any, are you ready to make?
• What should we write down so we do not lose it?

What has been useful in how we have been working, and what has not?

Be specific. A clear answer helps the two of you adjust.

• Which conversation do you still think about?
• What have we spent time on that you would skip next time?
• What do you want more of from these conversations?

Where have we kept going on a direction you no longer trust?

Say it straight. You can correct the plan without blaming the earlier choice.

• What do we keep returning to that no longer fits?
• What assumption would you like dropped?
• How should we bring it up if it shows up again?

What do you want kept between us, and what are you ready for someone else to know?

A direction sometimes waits until one other person hears it. Decide that before you set up the talk.

• Who already knows what we are working on?
• What are you not ready to say outside this room?
• Who would it help if they heard the update from you?

How would you like the written record of this work to read today?

A few lines in your own words are enough. You can revise them next time.

• How would you describe the direction in a short note to yourself?
• What have you ruled out?
• What is still open?