Questions to Ask When Meeting a Potential Client for the First Time

When I meet a potential client for the first time, they have often not thought about my services at all. They’re simply frustrated with something in their current setup (often lack of results from inbound marketing) and want to vent about it.

The first meeting isn't about making a pitch. It’s about asking the right questions, listening intently, showing empathy, observing their behaviour, all while giving subtle signals of your expertise. Giving them a particular solution comes later, after they start seeing you as a partner in their epic quest to defeat their challenge.

Over the past month I started consolidating all my notes from early client meetings, trying to find the right questions that I should always ask. I’ve identified 8 questions that, when integrated naturally into the conversation, seem to drastically increase the chances of a project actually happening.

Note: This is used for consulting services but a very similiar progression of questions can be used if you’re doing problem validation while you still don’t have a product.

Question 1: Tell me what you do at [company].

While acting as an ice breaker, the real purpose behind this is to find out the general context in which your lead is operating. You can also find out a lot, very early, about who is actually signing off decisions that impact budget, just by listening to cues about the internal team hierarchy.

Question 2: Why are you here?

Elicit the problem they’re facing in their own words to get a better understanding of what they consider crucial to their work. If they stall or their answer lacks clarity, you can get them to elaborate by asking: “what is the most important challenge you’re facing right now?”

Question 3: Why is solving this challenge important?

Here, we want to identify the motivators driving their decision to seek help. Try and understand if they’re driven by negative emotions (e.g frustration) or positive ones (e.g ambition). If their answer fails to bring bring this out clearly you can try asking: What will be the most positive impact of solving this challenge? Their answer is what you’ll build your pitch around.

Question 4: What is the most problematic aspect of dealing with this challenge?

If their motivators are based on negativity / frustration, you have to weed out the fluff and cut to the biggest issue preventing them from solving it themselves ( lack of skills or knowledge, lack of time, or lack of resources.) If they’re motivated by wanting to improve, you can consider asking them “If you had no limits, how would you boost your current resources in order to achieve this?”

Question 5: Who will benefit the most from solving this challenge?

The client might be wrong at this stage (it’s your job to educate them), but it’s important that you understand their perception of the biggest beneficiaries of solving the challenge: these are your stakeholders. Is it something that will boost team happiness and productivity, increase customer satisfaction, or directly impact sales?

Question 6: What options have you considered for tackling this challenge?

It’s very rare that people immediately look for an outside supplier without trying some other approaches first (for instance, hiring someone, training existing staff, or a SaaS solution). Understand what they’ve tried already, why those approaches failed, and what they learned from the experience.

Question 7: If you decide on a solution, what internal challenges will you face to make it happen?

At this early stage, it’s important to find out what stumbling blocks your lead will face once your solution is chosen (such as a difficult boss, lack of education about the issue, a risk-averse culture) so you can help them overcome these obstacles (or politely decline the project before putting too much effort in something that would never fly.)

Question 8: Are there any other challenges you’re facing?

It’s easier to sell to someone you’ve already sold to, and this question allows you to assess potential up-selling opportunities early on. It’s also helpful to ask why these challenges are not as urgent, so you can identify blind spots the client might not be considering, allowing you to highlight your expertise further.

It seems that the key is to ask non-leading, open ended questions that encourage candidness. It’s not about always using the exact phrasing or using the questions in the right order. You can skip questions if you have the information you need already, or if you don’t you can rephrase a certain question until you can move on to the next one.

With the information gathered, you should have enough ammo to understand how you can add value to the person in front of you. The next step is to convince them that you’re the right person for the job.