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What would it feel like not just having great and engaging meetings with clients but being able to become true business partners? Progressive MSPs has been started because when the Quarterly Business Review (QBR) meetings aren’t focused on the “Client’s Business Review” but the “MSP’s Business Review” then engagement drops and the relationship gets mired in the technology partnership level. Although it raises a concern about the scalability of the process - as account manager employees seem to have trouble engaging executives with real business discussions - there are best practices that can be applied to empower employees to elevate the conversation.

In this blog we collected five great conversation starters that will generate huge engagement among high-value client business owners and executives. Your growth need not stagnate just because you as a business owner are the only one who can deliver these meetings.

Upsell your clients with strategic QBRs and IT strategy meetings


Prerequisites for making business conversations easy

We have been teaching, coaching and guiding MSPs to do better consultative sales meetings, quarterly business reviews, audits and annual strategy workshops. We have researched what types of questions work and what questions won’t engage executives.

There are seven common traits among great questions that can elevate your conversations. You can read later five of our favorite questions, but we wanted to empower you to be able to create your own sets of questions later.

  1. Leading. Questions are open-ended and generally based to help the interviewer drive the conversation without need of great expertise in the topic.
  2. Low-risk. Whoever answers the question feels no pressure or risk of being intimidated or sharing information that would not be shared openly anyways.
  3. Trust building. Show honest curiosity and make the interviewees feel understood.
  4. Contextual. Relevant in multiple potential contexts. Questions can be asked in annual meetings, quarterly meetings or even in ad-hoc social events.
  5. Discovery. Ensure you take notes and go deeper when needed.  The answers can be used for general purposes or follow-up later with more information.
  6. Actionable. Drive specific actions or generate complete action plans from the answers and topics.
  7. Consultative. Ensure you conduct business and consultative conversations rather than promoting technology or solution specific outcomes. 

If the questions you ask executives are missing one or more of these traits then the result can be stalled conversations, uncomfortable feelings, and lost confidence.

Ok let’s dive into the questions one by one:


1. What made you successful in this business in the first place?

This question leads you to uncover the client’s main value proposition. That means they will talk about what distinguished them among their competition, why they started the business and what made them successful in the first place. This makes most executives proud as this is their story.

You can lead the questions towards the relevance of these aspects today. What puts their success at risk? How do they keep being successful in the future? Those avenues can help you to find potential business issues your company can help solve, either in the short term or in the longer-term.

2. What does your team do every day to keep clients happy?

This question leads to discovery of the core functions they have to do well to run the business. The team’s required focus on the critical things has to be maintained in order to keep clients happy. This is more important than ever as the competition is getting fierce in every industry.

That information gives you many clues of different operational challenges, bottlenecks and potential headaches for the executive. You can find initiatives they are working on and can capture important priorities you might be able to address with tech solutions.

3. What are the three things in your market that would not be relevant in the future?

This question leads to the future. What’s not going to be important in the future will reveal what will be important tomorrow. This is really a hidden strategy related question uncovering their perspective of future priorities.

That information gives you clues about how they see how technology itself will shape their industry, and how digital transformation is affecting their industry and company. You can understand what role they are giving to their technology initiatives. That gives you a great overview about what level they value your company’s help.

4. If you could work only one day a week, what are the critical things you would need to do to maintain the company?

This question leads to understanding their personal priorities. If they would have only one day to work a week, what roles and activities would they choose. This personal question can reveal many personal priorities. Also, it can be used to put in a negative order. See what types of work, obligations or roles they do not like. 

As an example, if they would answer: “I wish I would not have to do any cash flow management ever again” that can help you to see it’s a personal pain point for them. Or they may think about the core roles they play in the organization. 

This question is not an obvious one and very challenging. People usually do not have a quick answer for that but it can also unlock their personal goals with the company.


5. What habits do you want your leadership team to obtain

This is also a great question to unlock leadership gaps. Now, most executive’s main priority is to build a great leadership team. This question is focusing on the potential gaps the leadership team sees. 

This can help you to understand the personal leadership priorities and the leadership issues preventing them from growing - common needs such as better meetings, more accountability, better motivation or personal development. This will give you many clues to the pain points the leader has with managing and building a team. 

3 Steps to make this work

In the technology sphere most account managers, technical account managers, and vCIOs are engineers at heart and sometimes these types of conversations don’t come easy.

However, being in a comfort zone means going back to a technology conversation that is comfortable for the account manager but not engaging to the client.

Based on hundreds of sessions we have learned that confidence is everything when it comes to client meetings. Nobody wants to be in a situation where they don’t feel competent, confident and in control. Let’s follow these three steps to apply these questions to your next meeting. 

  1. Read aloud and tweak it until you feel authentic. Make sure the questions are comfortable to ask and natural to you.
  2. Think forward, what types of answers you might get and what would be your response to dig deeper or to switch the topic.
  3. Call 3-4 friends, team members or even your CEO and include these questions in your natural conversation. Listen and see what happens.

This skill will change the type of conversations you have with business executives and can transition you from being a great technical gifted account manager to a very assertive business consultant.


On a bumper sticker

Think about the following briefly:

  • Think about how many times you are covering these types of topics with your clients? 
  • What you are missing out by not having these discussions?
  • What are the obstacles preventing you to put these questions into your client meeting agenda?
  • How would you be perceived when asking these types of questions as a technology provider?
  • What is your comfort level to lead conversations in these points?
  • What would you get by having these business-related conversations?

The more you and your team are getting comfortable diving into your client’s businesses the more opportunities, loyalty and trust you are going to obtain. Put together your own versions of the questions, tweak them and make sure you are becoming a high-value business partner by helping your clients as best you can.

Sign up for the Client Engagement Excellence Manifesto PDF coming end of January

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