Clients and Colleagues: Asking the Right Questions

Questions play a crucial role in any business. Deciding whether the job applicant in front of you is a star performer or a sociopath (or anywhere in between) can be a challenge. Navigating a client meeting with curiosity and professionalism, getting all the information you need, working out the hidden pitfalls, all whilst managing expectations of those around you, requires strategy and cunning.

This guide aims to give you the ultimate questions you should be asking clients and colleagues. These are quietly effective queries that will always deliver debate with insightful, important answers regardless of who you are talking to

1. What do you call success?

If you do not know this, then you cannot possibly hope to succeed. For a client it could be brand awareness, pageviews or profit. For a colleague it could be education, efficiency or euphoria. For me, success is alliteration (can you tell?). A clear vision for success allows everyone to work towards the same goal, as well as providing a useful reminder of why you’re doing what you’re doing.

Pair people together who want the same thing and you are on to a winner.

2. Other than for the money, why are you in business?

If the previous question returns the response “money!”, then you’ll need to dig a bit deeper.

From a client, the answer to this question can end up becoming the core message of content strategy or a whole new set of recommendations for future direction. For a colleague, it might be to make people happy, to do a good job, or even to get to know a new city. If you know this, its much easier to give people work they love and to delegate fairly and effectively.

3. Are you going as fast as you would like to?

Expect the answer for this to be “no”, as it brings to light any frustrations your client or colleague may be feeling. Then ask why. If you can solve the why with tactics and strategies, you become invaluable. For a colleague the answer will also almost certainly be no. Again, ask why, then do something to make things better. It will most certainly improve your bottom line, keeping yourcolleagues and your company happy.

People around a table asking questions

Taking the time to ask questions is a crucial part of managing clients and colleagues.

4. Why are you doing this now?

For a colleague or a new starter, this question can often reveal what makes them tick. It is an insight into their state of mind, their priorities and their workload, which is all good stuff to be aware of. For a client, this is the context question. You need to understand their business direction to make yourself as useful as possible.

5. How do you make decisions?

The big split is data vs gut. People can fall pretty hard on one side or the other. Check out our very own Sam Nemzer’s thoughts. He doesn’t hold back…

The key here is to know what a client wants to see. Do they want a bulletproof graph to back your advice or a set of testimonials from happy clients and examples of previous successful campaigns so they know they can trust you?

6. What limits you?

If you can solve this problem, you can be a hero in the eyes of your colleagues or clients. It’s no mean feat, but in doing so, you’ve accomplished something that nobody else in their professional life has been able to do.

7. What is exciting for you right now?

For the client, you need to be doing everything you can to tap into this. For a colleague, explore what’s possible and help them to run with it; You’ll probably find they’ll be more focussed and productive. The reason that this question can be so useful is because passion is what keeps people up late and coming back for more. Money is no substitute.

Some of the best work gets done when you are allowed to do what you want. Just ask Google.

Distilled Manifesto Part 1

The very first sentence in the Distilled manifesto proves the need for questions.

8. Why?

This one may be a cheat, but it is the one question that still needs asking (often after you’ve asked one of the previous questions). It’s useful because it forces colleagues and clients to truly question their own perceptions. Harness your inner inquisitive child and get to the bottom of the issue.

9. How?

After why comes how. How can it be faster? How can it be easier? Maybe you can offer some tactics. Maybe you need a whole new strategy. How allows you to see what is actually achievable and the way in which it should be achieved.

10. Silence

OK, so it’s not strictly a question, but just stop talking and see what happens. Don’t ask the follow up question. Just shut up.  

In silence, most people talk, and many open up. When given time, people offer more than they ever could imagine. Jeremy Vine makes that exact point when I interviewed him recently: “Sometimes if you just leave a gap, the next thing they say will be much more interesting.”


There you have it. This isn't an exhaustive list, so feel free to add any of your own killer questions in the comment section, or get in touch on Twitter. These questions are, however, a go-to list when you know you need more information, because they each lead your colleague or client to think in a way they probably wouldn’t if you hadn’t reached out in the first place.

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