Questions to Ask in a Mastermind Group
For members and facilitators of a mastermind group: a handful of business owners or peers who meet on a schedule and give one member at a time the whole table's attention. The list runs in the order a meeting does, from the opening round through the hot seat, the attempts and options, what is being avoided and the commitments, and it ends with questions about the group itself. Most are put to the person in the hot seat, and a few go to everyone in the room.
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The questions
Each question, and why to ask it
Opening round
What is your biggest win since we last met?
Why ask it
Keep each answer to about a minute so the opening round does not eat the hot seat. The useful follow-up is 'what did you do that caused it?', since a win with a cause can be repeated by someone else at the table. A member with nothing to report two meetings running may need the hot seat more than whoever is booked for it.
What did not go to plan since we last met?
Why ask it
Ask it straight after the wins so the round is not a highlight reel. One sentence each, with no fixing from the group. Two members reporting the same miss have handed the facilitator a topic for a future meeting.
What did you commit to last time, and did it get done?
Why ask it
Read the commitment back from the notes, not from memory, because the remembered version is usually the smaller one. Done, partly done or not done is all the round needs, written next to the original line. Reasons can wait for the hot seat or a quick word afterwards.
How far along are you on the goal you set for this quarter?
Why ask it
This only works when every member has one goal written in the group's notes, for a quarter or whatever stretch the group plans in. A rough answer such as 'about a third' is enough, followed by what would get it back on pace. A goal that no longer fits can be changed out loud here, which beats letting it fade from the notes.
What are your numbers since the last meeting?
Why ask it
Have each member choose one or two figures when they join, such as revenue, new leads or cash in the bank, and report the same ones every time so the group sees a trend and not a highlight. Someone who would rather not share real figures can give the change against last month. When a member quietly stops reporting a number, ask about that number.
Which number moved most, and what do you think moved it?
Why ask it
A figure alone tells the table little, while the member's theory of why it moved is something the others can test in their own businesses. 'No idea' is an honest answer and a fair hot seat topic, since working out what to measure is a job a group does well.
What did you learn since last time that someone else here could use?
Why ask it
This is where a mastermind pays for itself between hot seats: a supplier, a pricing test, the wording that got a late invoice paid. Ask for the specific thing, with the name or the exact line, and put it in the shared notes. Skip it on a day when the round is already running long.
How are you doing, apart from the business?
Why ask it
Owners tend to answer 'how are you?' with company news, so the second half of the question matters. Take the answer and thank them without solving it, and let one member check in privately afterwards when it sounds heavy. A peer group is not a counselor, and it should say so when something is beyond it.
Does anyone have something urgent that cannot wait for their turn in the hot seat?
Why ask it
Put it to the whole table at the end of the opening round. A decision due this week, such as an offer to accept or a hire to confirm, can be given ten minutes without displacing the member who is booked. At most meetings the answer is no, and a second opinion on one email can wait until the main session is over.
The hot seat
What is the one problem you are bringing to the group today?
Why ask it
One, not three. A member who lists several is usually unsure which matters, so ask which they would pick if the group could only fix a single thing. Have them say it in two sentences before any background, and write it where everyone can see it.
Can you put that as a question the group could answer?
Why ask it
'Sales are slow' is a complaint, and 'Should I hire a salesperson or raise prices first?' is something six people can work on. A member who cannot make that turn yet deserves the first ten minutes spent on it, because sometimes finding the question is the whole session.
Why this problem now, ahead of everything else on your list?
Why ask it
The answer shows whether it is urgent, important or only recent. A deadline, a resignation or a bank balance makes a clear case. If the reason is 'it has been bugging me', ask what else is on the list, since the bigger item may be sitting just under it.
What does the group need to know about the business to give you useful advice?
Why ask it
Ask for the facts that change the advice: team size, price point, margin, how customers arrive, how much cash there is to play with. Give it three minutes and cut off the company history. Members who keep asking for background halfway through are telling you this step was rushed.
What would be different three months from now if this were solved?
Why ask it
A concrete picture, such as two free days a week or a waiting list, gives the group something to aim its ideas at. It also tests the problem: an answer of 'not much, really' suggests the member has brought a symptom, and the next thing to ask is what sits behind it.
What is it costing you each month it stays unsolved?
Why ask it
Money, hours or sleep all count, and a rough figure is enough. The cost sets how much the fix is allowed to cost, which rules ideas in and out quickly. A member who cannot name any cost may be working on something that feels urgent and is not.
Is this a decision you have to make, or something you do not know how to do?
Why ask it
The two call for different help, so settle which it is before the advice starts. A decision wants the options laid side by side and someone to argue the other way. A skill gap wants a member who has done it, a referral, or a view on whom to pay.
Who else has a say in this: a partner, an investor, a key employee, someone at home?
Why ask it
Advice that ignores the co-founder who must agree is wasted. Find out whose yes is needed and whether that person knows the question is being discussed here. Quite often the commitment that comes out of the session is simply to go and have that conversation.
What kind of help do you want from us today?
Why ask it
Offer the choices out loud: ideas, holes poked in a plan already made, an introduction, or the thing nobody has been willing to say. Asking first stops the room from brainstorming for someone who came for a verdict. Check again halfway through, since what they want can change once they hear the first responses.
If one of us brought you this exact problem, what would you tell us to do?
Why ask it
People are clearer about a friend's business than about their own. Whatever they say is often their real answer, and the next thing to ask is what makes it harder to follow in their own case. Use it early: it can save the group twenty minutes of advice the member already has.
Attempts and options
What have you already tried, and what happened each time?
Why ask it
Get the full list before anyone offers an idea, or half the suggestions will be met with 'we did that'. For each attempt ask how long it ran and how they judged it. Two weeks of a new ad or one awkward sales call is a test that was stopped, not a method that failed.
What worked a little that you stopped doing?
Why ask it
Most businesses have one: the newsletter that brought in two clients, the follow-up call that got dropped in a busy month. Restarting it is cheaper than anything new the table will invent. Ask why it stopped, because that reason will stop it again.
Which options are on your list, and which one are you leaning toward?
Why ask it
Hearing the lean saves the group from arguing for a choice that is already half made. Ask what would have to be true for the favored option to be right, and let members test those conditions. A list with a single option on it gives the group its first job, which is to add a second.
What advice have you already been given on this, and why have you not taken it?
Why ask it
An accountant, a spouse or a coach has probably weighed in already. Why the advice was not taken is more useful than the advice: too expensive, too slow, or from someone who does not know the trade. Tax, legal and employment questions belong with those professionals, and the group can say so plainly.
Who here has been through something like this, and what did you do?
Why ask it
This one goes to the table, not to the hot seat. Ask for what each member actually did and how it turned out, told in the first person, because a story can be taken or left while 'you should' has to be argued with. When nobody has been there, say so and ask who the group knows who has.
What are we all assuming that might not be true?
Why ask it
Put it to the whole group once the advice starts to agree with itself. Common ones are that customers will not pay more, that a key person cannot be replaced, or that the owner has to be the one doing the work. Pick the assumption that would change the most if it were wrong and ask how it could be checked cheaply.
What is the smallest version of this you could test in the next two weeks?
Why ask it
Big fixes stall between meetings, and small tests come back with results: one new price quoted to three customers, one job ad, one landing page. Ask what result would make them go further and what result would make them drop it. Write both down before the test runs.
Being avoided
What do you already know you need to do?
Why ask it
Plenty of hot seats end at an answer the member walked in with, and asking for it directly, once the facts are out, can shorten the session. A member who names it at once has changed the group's job from finding the answer to finding out what is in the way.
What conversation are you putting off?
Why ask it
There is nearly always a person in it: an employee who is not working out, a client who pays late, a business partner. Ask who it is and what the first sentence would be. Members can help draft that sentence on the spot, which is sometimes the push that was missing.
What would you do if you were not worried about how it would look?
Why ask it
Closing a location, dropping a well-known client, taking a job for a year: pride keeps some options off the list. Saying one aloud is not agreeing to it, and it lets the group weigh it with the rest. A good follow-up is 'whose opinion are you picturing?'
What is your own part in how this came about?
Why ask it
Ask it kindly, and only after the member has felt heard, or it lands as blame. The point is practical: the part that is theirs is the part they can change by Monday. An owner who answers 'I hired too fast' or 'I never said no' has usually found the commitment for next meeting.
Is this the real problem, or the one that is easier to talk about?
Why ask it
A hiring question can be covering a cash question, and a marketing question can be covering doubt about the whole offer. Raise it when the answers so far have felt thin, and leave a silence after it. Whether to switch to the bigger problem now or bring it next time is the member's call.
What have you brought to this group before that is still not done?
Why ask it
The notes will show it: the same hire, the same price rise, the same difficult partner, three meetings apart. Naming the pattern is not a telling-off. It lets the group stop offering new ideas and ask what makes this one so hard to act on.
What are you tolerating that you know is costing you?
Why ask it
A late-paying client, a messy set of books, a staff member everyone works around. Things like these rarely feel urgent enough for a hot seat, which is how they last for years. The question also suits a round where each member names one, on a day when nobody has a topic ready.
What is each of us thinking about this and not saying?
Why ask it
For the group, near the end of a hot seat that has stayed polite. Go around and take one sentence from each person, starting with whoever has spoken least. The facilitator should ask the member first whether they want it, and stop the round if candor turns into piling on.
Commitments
What are you taking away from this, in a sentence or two?
Why ask it
The member chooses, not the group. Hearing which idea landed tells everyone whether the session worked, and the pick is sometimes a passing remark and not the idea that got the most airtime. No takeaway at all usually means the problem was not framed tightly enough, which is worth knowing for the next hot seat.
What will you commit to getting done before our next meeting?
Why ask it
It should be something the table can check: three candidates interviewed, the price list sent, the lease signed or turned down. 'Work on hiring' is a topic, not a commitment. Record it in the member's own words, because those are the words that get read back in the opening round.
What is the first step, and which day will you take it?
Why ask it
A commitment four weeks out tends to get started in week four. A first step with a date in the next few days, such as 'email the landlord on Thursday', gets it moving while the session is fresh. Ask them to put it in their calendar before the meeting moves on.
What is most likely to get in the way, and what will you do when it does?
Why ask it
The member usually knows: a busy season, a partner who will object, their own habit of researching in place of deciding. Plan for that one obstacle now. It also gives the group something specific to ask about next time besides 'did you do it?'
What will you drop or hand off to make room for it?
Why ask it
A full week does not gain six spare hours because a meeting went well. Unless something comes off the list, the new commitment is the thing that will slip. An honest answer here sometimes shrinks the commitment, and a smaller one that gets done is the better result.
How do you want us to hold you to it before then?
Why ask it
Some members want a message at the midpoint, some want a partner from the group, and some want to be left alone until the meeting. Agree who does what and by which day, or nobody will. Ask too what they want to hear if they miss it, which is easier to settle now than afterwards.
What do you need from one of us before we meet again?
Why ask it
An introduction, a look at a proposal, a copy of someone's onboarding checklist, twenty minutes on the phone. Let members volunteer and name a date. Offers made across the table and never followed up wear down trust faster than a missed commitment does, so note them like any other.
The group
What does each of us want from this group over the next year?
Why ask it
Ask it at the first meeting and again every year, and write the answers down. One member wants accountability, another wants introductions, a third wants somewhere to think out loud, and a format built for one will frustrate the others. Reading last year's answers back is the fairest test of whether the group delivered.
What was the most useful thing that happened in this meeting?
Why ask it
Make it a one-minute closing round at every meeting. Over a few months the answers show what the group is good for, whether that is the hot seat, the numbers, or the ten minutes of talk before the start. Thin answers several meetings in a row are the cue to ask whether the group is still worth everyone's time.
Is this group still worth the time you give it?
Why ask it
Ask it on a schedule, perhaps once a quarter, so that it is routine and not an alarm. Have people answer in writing first so the loudest opinion does not set the tone. A member who says no has done the group a favor, provided the next thing asked is what would change the answer.
Are we honest enough with each other, or have we become too polite?
Why ask it
Groups whose members like each other drift toward encouragement. Ask each person for a time they held something back in a hot seat and what stopped them. One or two of those examples usually turn out to be advice the member wishes they had heard.
Is everyone getting a fair share of the hot seat?
Why ask it
Check the record, not the feeling: who sat when, and who has passed more than once. A member who keeps giving up a turn may be modest, or may not trust the group with the real problem. A rotation on the calendar fixes the first, and a private conversation is the way into the second.
What was said today that should not leave this room?
Why ask it
Many groups run on the rule that everything stays inside, and it still helps to hear a member flag the specific thing: a sale in progress, a staff problem, a personal matter. Agree the rule when the group forms and repeat it when someone new joins. A matter that needs more than a promise, such as a signed agreement, is one for a lawyer and not for the group.
What should we change about how we run these meetings?
Why ask it
Length, frequency, online or in person, how long the opening round runs, who keeps the notes. Take one change at a time and try it for three meetings before judging it. In a paid or hosted mastermind some of this is the organizer's call, so ask how changes get made there.
Do we have the right mix of people, and is anyone missing?
Why ask it
Many groups find they work best when members are at a similar stage and not in direct competition, and that can shift as businesses grow. Talk about the seat and not the person: what experience would help, and how a new member gets proposed and agreed. With someone who has outgrown the group, a direct and kind conversation outside the meeting is fairer than hints.
What do we do when someone keeps missing meetings or commitments?
Why ask it
Decide the rule before it is needed, for example a private check-in after two missed meetings, so that it never has to be invented around one person. Ask the member what is going on before assuming they have lost interest. Sometimes the right outcome is a pause with a date to come back, and the group should be able to offer one.
How to run these questions in a mastermind meeting
Practical guidance for the conversation itself
Building the agenda
A ninety-minute order
For a group of five or six: fifteen to twenty minutes on the opening round (win, last commitment, numbers), two hot seats of about thirty minutes each, then ten minutes for commitments and a closing round. A larger group or a shorter slot means one hot seat, not three rushed ones. Whatever the lengths, say them at the start and have someone other than the facilitator watch the clock.
Book the hot seat ahead
Put names against dates a few meetings out, so nobody is choosing a problem in the parking lot. Leave room to swap when a member has something urgent, and keep a note of who gave up a turn so it comes back to them.
Ask for the problem in writing
Two or three lines sent to the group a day or two before: the question, the key facts, what has been tried. Members arrive having thought about it, and the hot seat can start at the questions under Attempts and options instead of at the background.
Keep one set of notes
A shared document holds each member's tracked numbers, the commitment they made and whether it was met. It takes five minutes a meeting, and it is what keeps the opening round honest. Rotate the note-taking so it does not fall to the same person every time.
Running a hot seat
Questions first, advice second
Split the time roughly in half. In the first half the group may only ask, working through The hot seat, Attempts and options and Being avoided. Advice given in the first five minutes is usually aimed at the wrong problem, and the member has often heard it already.
Pick six or seven, not the whole page
Nobody should face every question here in half an hour. A workable set: the one problem, the question form of it, what the group needs to know, what has been tried, what they already know they need to do, and the commitment. Add others when an answer opens a door.
Speak from experience
'When my best technician left, I did this, and here is what it cost me' gives the member something to weigh. 'You need to let him go' gives them something to resist. A facilitator can ask anyone who starts with 'you should' to say where they learned it.
Let the member go quiet
Once the ideas are flowing, the person in the hot seat does best by writing them down and not answering each one. Defending the current plan against every suggestion uses up the time. Their response comes at the end, when they say what they are taking away.
The facilitator's three jobs
Keep the time, keep the group on the question that was asked, and bring in whoever has not spoken. In a group with no paid facilitator, rotate the role, and do not chair on the day you are in the hot seat yourself.
Between meetings
Send the commitments round the same day
One message lists each member's sentence and date, taken from the notes. It removes any doubt about what was promised, and it gives the next opening round its script.
A midpoint line
Halfway to the next meeting, each member posts one line in the group chat: on track, behind, or done. It takes a minute, and it gives someone who is stuck two weeks of help in place of an apology at the meeting.
Follow through on offers
Introductions and document reviews promised across the table should carry a name and a date like any commitment. The facilitator can read them back in the opening round along with everything else.
When the group stops working
The opening round takes half the meeting
Use a timer and a fixed order: win, commitment, numbers, three minutes a person at most. The other opening questions are for days with time to spare, and anything that needs discussion is parked for the end or becomes a request for a hot seat.
The same problem keeps coming back
When a member brings the same issue a third time, stop offering ideas. Ask the questions under Being avoided, and consider whether the commitment has been too large each time. Some problems belong with a coach, an accountant or another professional, and the group can say that.
Advice turns into a pitch
Members sometimes sell to each other: a service, a course, a referral they earn from. Agree a rule early, such as saying so out loud whenever you would benefit from your own advice, and let the member in the hot seat decide whether to take it further outside the meeting.
Everyone agrees with everyone
A group that has met for a year can turn into a circle of encouragement. Assign one member per hot seat to argue the opposite case, or ask what each person is thinking and not saying. If that still produces nothing, a new member or a guest may.
In a paid or hosted mastermind
Fees, who is admitted, how hot seats are allotted and what the host keeps confidential vary from one program to the next. Ask the organizer how each of those works there before you join, and ask a current member whether the meetings match the description.