If you know me or have ever interacted with me professionally, you’re probably aware of a certain reputation that I have: I like to ask questions. Lots of questions! I do this not to be annoying – though I’ve been told at times it can be – but to gain as clear a picture of the current situation as I possibly can. I’m also just naturally inquisitive. I want to know more about the people I’m speaking with – what they do, what interests them, where we may have some common ground or areas where we can help each other. Mostly, I want to know who they are.

Asking questions comes more naturally to some people than others, but in all cases, it’s important to know how to ask good, probing questions, especially in a business networking environment. While I’ve always liked to ask questions, I’ve had to train myself to ask the right questions in the right way to improve my chances of having an interesting, productive discussion – which is the subject of this edition of The Friedman File.

The Importance of Asking

Management consultant Peter Drucker said, “The most serious mistakes are not being made as a result of wrong answers. The true dangerous thing is asking the wrong question.” Though this may come off as too ominous a warning for A/E/C firm leaders trying to encourage their people to learn the proper questions to ask and how to ask them, Drucker’s quote nails an important fact – we spend far too much time worrying about the answers we’re going to give than we do on the questions we should ask.

A basic tenet of business development that I fiercely believe in is to talk less and ask more. This is a clear path to better understanding the pain points that your clients and prospects face, which in turn helps you establish a rapport and build credibility with them. By formulating your questions strategically, you can move the conversation in the direction that you want to take it, better influencing their knowledge and perception of you and your firm. Asking good questions is also essential for assessing client satisfaction and creating opportunities for new and repeat work, while garnering intelligence that enables you to customize your BD approach and messaging.

How to Ask

Much of the art of asking good questions the right way lies in how you view the relationship. Is your purpose for speaking with someone simply a means to an end, or do you truly have their best interests at heart? (While we’re talking about business networking here, this often holds true of any conversation for any reason!) The more you move your mindset toward the latter, the more likely you are to genuinely and spontaneously ask beneficial, positive questions that lead to a productive outcome.

One important tip to keep in mind is that open-ended questions tend to yield more robust answers. For example, “What are your greatest challenges right now?” Or “What do you know about our firm?” If you’re speaking with someone about a pending project, ask “How will you define the success of this project?” and “What most concerns you going into this project?”

Asking open-ended questions offers you a better understanding of your client or prospect. It helps you gather intelligence that can inform the business development process and lead to strong, long-lasting relationships. This is also the best way to gather feedback on project performance, while identifying future needs and opportunities.

Asking open-ended questions gives the other person the leeway to expand the discussion into areas you hadn’t expected or known about. And it’s more likely to lead to something that should be a goal – having them turn the discussion around to ask you questions about yourself or your firm. As a result, it’s important to remember that this is a dialogue, not an interview. So while preparing the right questions is critical, it’s equally necessary to be prepared to talk about yourself and your firm in the context of the discussion. So have that elevator speech ready.

What to Ask

Researching the people you’ll be talking with – or potentially talking with – is a vital tool that leads to the best questions to ask. Search the public domain, such as on their firm’s website, on LinkedIn (both the individual’s profile and their employer’s LinkedIn page) or other social media, or through internet queries. You can find a lot about a person by simply typing their name and a few details in the search bar.

It’s also helpful for people who are uncomfortable asking questions in business networking settings to practice their technique in places where they feel more at home. Like at a club, community event, or peer networking event. I encourage A/E/C professionals to join and participate in trade groups as a training ground. It’s amazing how easily people can learn the art of asking good questions through diligent practice.

It’s also important to keep in mind the purpose of your discussion and to establish goals in advance. Are you just trying to make an initial contact that you hope to cultivate later, or is there a specific opportunity that you’re interested in pursuing?

Here are four situations that you or your colleagues may find themselves in, along with some sample questions you can ask. Remember, ask questions in your own way and in your own voice; otherwise it may seem awkward or phony.

To Better Understand Your Client’s or Prospect’s Universe. What are your company’s/organization’s goals for 2024 and beyond? What role do you envision playing in achieving these goals? What key drivers (e.g., technological, economic, demographic, regulatory) do you see most impacting your industry? What are some examples of recent successful projects? Why were they successful?

Pre-Qualifying/Gathering Pre-Proposal Intel. What most concerns you going into this project? What’s the timeframe for this project? Does this project have funding approval? Tell me more about your budget constraints for this project. Who else besides our firm are you considering?

Gathering Feedback on Project Performance. What could our firm be doing better with respect to understanding your needs, the quality of our services/deliverables, and project communications and responsiveness? What feedback have you received from users on the project? What additional advice/feedback do you have for us on our performance?

Identifying future needs and opportunities. What do you see as your company’s/organization’s greatest upcoming needs/challenges? What opportunities exist for our firm to share case studies, best practices, and lessons learned with your company/organization? Can we present an in-house lunch-and-learn for you and your colleagues?

Putting Your Questions Into Practice

Doing your research and having questions at the ready is essential, but knowing how to “work” the conversation is equally important. One approach I recommend is to start the conversation with broader, more innocuous questions to build the rapport, and then begin to zero in more on the areas that lead you to learn the most vital information and achieve your goals. For example, when gathering pre-proposal intelligence, save the questions that appear to be most self-serving until the end, after you’ve reached a certain comfort level. When identifying future needs and opportunities, don’t neglect to ask the “closer” questions, but wait until the time is right. Examples include, “How would you like me to follow up with you?” “Who else do you recommend we meet with in your company?”

Ultimately, you’re in the conversation for a reason. There’s nothing wrong with serving your business purposes while also showing an interest in the person you’re talking with.

Ultimately, you can learn to ask the right questions if you approach the conversation from a genuine place of curiosity, research well and practice often. You can start today by checking in with some current and past clients, and by setting up opportunities for your staff to learn these techniques and then practice them at lunch-and-learn sessions.

What questions do you have about this topic? Write me at rich@friedmanpartners.com or call me at (508) 276-1101. If you’d like to hear more of my thoughts on the subject, I’ll be presenting “The Art of Asking Probing Questions to Boost Client Satisfaction and Increase Your Win Rate” as part of Unanet’s webinar series on October 11, 2023 (mark your calendar!).