5 great questions to ask to really understand your client’s business

I love the start of a new year. Not just because it always means I will be skiing in knee deep powder in Whistler, the best place in the world (which I am, hence the photo above just to rub it in), but because the beginning of a new year is the best time EVER to shift your client relationships.

Why? Because the new year gives you the perfect excuse to ask them all sorts of longer-term, big picture questions about what the year ahead holds – for them personally, for their team, their company, even their industry. And it’s these kinds of conversations that are going to show you’re interested in them and their world, not just what money they’re going to give you, which will potentially shift your relationships from technical, social or ad-hoc, to a true trusted relationship.

To really get to know and understand my client’s businesses, here are five questions that I will often ask:

  1. “In an ideal world, what will your business look like in 3 years?” This not only shows that you care to understand the future of the business, and helps the client to think and reflect about the future which is always valuable, but by understanding this you can then help your client to prioritise their strategies.
  2. “What do you believe are the going to be the three most critical drivers of success in your business this year?”  This again forces the client to really think. And make sure you ask for three –  if you only ask for one thing you are likely to get the top-of-head response, but by asking for three they will have to think hard, and often it is the third which turns out to be the most important.
  3. “Would you mind letting me have a better understanding of your strategy?” I always like to ask permission before I ask them to share their strategy with me, if they haven’t already done so. Make sure you have already established a good level of rapport before you ask this – it’s not a question to ask in the first 10 minutes of meeting a new client.
  4. “What do you think are the three things that the business did best in 2015, and what are the three things it could do better in the year ahead?” This allows the client to have a balanced response, and shows that you are not unrealistically positive or negative. It will also help you to better understand the real triggers in the business and the sort of person the client is (opportunistic or risk averse) which will help you adapt your behaviours if needed.
  5. “By the end of the year, what would you like your competitors to be saying about your business?”  This is a question that a client will rarely, if ever, get asked, so you will really be making them think. That in itself is value for the client, but you might also get some extremely interesting reflections and insights from the client.

On the flipside, if you head into a meeting with the intent to better understand your client’s business but ask questions like the one’s following, I’m sorry to say that you won’t be shifting the relationship anytime soon. Expect to be asked for a few discounts and to lose work because of ‘price’ with this client in the year ahead!

  1. “From what I can see, my product/service will really help you with that strategy.” Remember that to be helpful and build trust, you need to keep your self orientation really low. Think about how you can help them with their strategy with ideas and connections that might not be related to you and your business in the first instance. This will show you’re not just there for a sale.
  2. “What will be your biggest challenge this year?” Remember when I wrote that I hate being asked about my challenges? Try to avoid this question…or if you must ask it, ask both sides of the coin instead – like question number 4 in my great questions to ask. Try to focus on the positive future instead of the negative past.
  3. “What projects do you have coming up this year?” I’ve added this one in because 9 times out of 10 when I hear this question asks it precedes a blatant sales pitch – and your client will feel this coming. Chances are this information will come out by simply asking some great questions about their strategy instead, so try to resist the temptation. And remember, when you’re a trusted partner, they’ll want you to know about every project they have.

Ultimately, your aim is to make your client think. If you just have narrow and short term questions you will probably get top-of-head responses and the conversation will just become a chat.  While this will be pleasant, it is not necessarily valuable to your client – and by the end of 2016, if I was to ask your clients what they think about you, I hope they tell me about how valuable you are to them and their business.


If you’d like to comment on this post or join the conversation, please head on over to the LinkedIn post where this was first published.