How to design work that actually works - 52 questions to ask your team.
The organisations that will thrive aren't the ones who predicted every change correctly. They're the ones who built a habit of listening.
Real listening. Not listening as a ‘management technique’. Not the kind of listening that happens in an annual survey that gets filed after the board meeting, but the kind that happens in rooms where people feel safe enough to tell the truth.
In nearly thirty years of working inside organisations the most valuable information I've ever found was already in the building. It was sitting with the people doing the work. The people who knew exactly where the friction was, where the system broke down, where the energy was being wasted.
It just hadn't been asked for.
The one habit that changes everything
I've seen leadership teams spend months on strategy away-days, culture programmes, and restructures, when the answer to what was actually broken was available in any team meeting, with the right question.
One honest question, asked regularly and genuinely, will tell you more about your organisation than any consultant's report.
Not "how is everyone?" Not "any questions?" The kind of question that creates a moment of real honesty. That signals to your team: I actually want to know. I can handle the answer. And I'll do something with it.
What's actually getting in the way?
That question alone has changed the direction of more projects, programmes, and organisations than I can count.
52 questions. 52 weeks. One year of honest conversations.
What follows is a full year's worth of searching questions - one for every week - grouped into five themes. You don't have to use them in order. Start with the theme that feels most relevant to where your team is right now.
Use them in team meetings, one-to-ones, or as a prompt for your own reflection as a leader. The only rule: be genuinely ready to hear the answer.
Culture & Honesty
What's the one thing nobody says out loud in this team - but everyone knows?
If you could change one thing about how we work together, what would it be?
When did you last feel genuinely proud of something we did here?
What do we say we value - and what do we actually reward?
Is there anything you're pretending is fine that isn't?
What would a new person notice about this team in their first week?
Where are we performing for each other rather than being honest with each other?
What feedback have you been sitting on that you haven't given yet?
What does this team do brilliantly that we never talk about?
When do people in this team feel most like themselves at work?
What are we tolerating that we shouldn't be?
Performance & Delivery
What is actually getting in the way of you doing your best work?
Where are we spending time on things that don't matter?
What's the most frustrating part of your week - and is it avoidable?
What process do we have that exists because it always has - not because it helps?
Where do we create work for each other unnecessarily?
What decision gets made too slowly here - and why?
What are we measuring that doesn't tell us anything useful?
If you could cut one thing we do to free up time for something better, what would it be?
Where do you feel most effective - and what makes that possible?
What would help you do your job better that you haven't asked for?
What's the one thing that if we fixed it would make everything else easier?
Change & Innovation
What's a better way of doing something we've always done the same way?
Where are we solving yesterday's problem instead of tomorrow's?
What would we do differently if we were starting from scratch?
What change have we made recently that's actually worked - and why?
What are we afraid to try - and what's the real reason?
Where are we moving too slowly and why?
What's something another team or organisation does that we could learn from?
What would make the biggest difference to the people we serve?
If we could only focus on one thing for the next 90 days, what should it be?
What assumption are we making that we've never actually tested?
What would we need to stop doing to make space for something better?
Leadership
Am I giving you what you need from me - and if not, what's missing?
When do you feel most supported by the leadership - and when do you feel least?
What decision have I made recently that you didn't understand or agree with?
Where am I getting in the way - even unintentionally?
What would you do differently if you were leading this team?
Are the priorities I've set the right ones - and do they feel achievable?
When did you last feel genuinely heard by the leadership here?
What do I do that gives you confidence - and what creates uncertainty?
If you could tell me one honest thing that would make me a better leader, what would it be?
Where does the leadership of this organisation say one thing and do another?
What would make you trust the leadership more?
People & Wellbeing
How are you actually doing - not the version you tell me, the real one?
What's making work hard for you right now that has nothing to do with the work itself?
When did you last feel genuinely energised by something you did here?
What would make coming to work feel better tomorrow than it did today?
Where do you feel underused - where could we be getting more from what you bring?
What does this team need more of to do its best work?
What does good look like for you in this role - and are we anywhere near it?
If you could design your ideal working week, what would it look like - and how far are we from that?
One last thought
These questions only work if you mean them.
Your team will know within seconds whether you're asking because you genuinely want to know, or because it's on the agenda. The quality of the answer you get is a direct reflection of the safety they feel to give it.
That's not a technique. That's leadership.
