12 Tips for Building Rapport with Business Leaders (Trends and Insights)

How do you build relationships with business executives? Often times your opportunity to shift from a fleeting, impersonal relationship with a senior business decision maker (BDM) to a more direct relationship stems from what you can do to build rapport and curiosity in a few unplanned moments.

For Microsoft Enterprise Architect Ron Lamb, the “win” is to gain interest from the BDM for a 1:1 meeting on a topic that is of great personal curiosity or challenge. You may have an unplanned meeting in a coffee room, elevator, or after completing a larger meeting. You have a few moments to create rapport and take the first steps in building a relationship that works on a new plane, one that transcends any specific initiative that you and Microsoft are working on at that moment. What techniques and patterns seem to work to gain that initial 1:1 opportunity, and then build upon it?

This post summarizes the experiences and observations of Ron Lamb, a Microsoft Enterprise Architect involved in business strategy planning.


Over the years I’ve expanded my services from technology into business-focused development and business strategy, especially as I’ve acquired more experience across many industries and around the world.

One of my career objectives has been to quickly build great relationships with chief executives and business decision makers during our engagements. Though my participation often begins as a subject matter expert or to help drive transformation, a personal connection creates opportunities to have a larger and broader impact, and perhaps even become a special resource to that executive. David Maister’s book “The Trusted Advisor” describes the opportunity and techniques best.

Increasing the Value of an Enterprise Architect

For me, an important part of creating rapport and building relationships is quickly opening the door for an exchange and testing of ideas, while presenting learnings from peers.

My goal is to help business executives walk away having learned something, with skills or insights that they didn’t have earlier. I want to provide individual value, in addition to the value I bring as a part of the project team.

In my short conversation with the executive, I share my focus on a challenge that I’ve been researching and struggling with and provide some provocative element of the challenge. I seek an indication that they are challenged / perplexed by the same thing, and if so, ask if perhaps I could invite them out for an opportunity to talk to them about it. I choose a challenge that I know the executive is also curious or concerned about. I share my understanding of the size of the challenge and the opportunity, the lack of a clear industry answer, and the risk of committing to a path that has a suspect likelihood of success. Business executives have a full plate of such highly unstructured, perplexing challenges, so perhaps not unsurprisingly, I often get a positive response.

The opportunity that I imply and hope an executive responds to, is an opportunity to:

  • Hear something new and thought provoking,
  • Have a chance to test out their own observations, beliefs and hypothesis,
  • Talk about something that never seems to land on their leaders’ or subordinates’ area of focus,
  • Discuss a “squishy” problem that they either currently or certainly will have to deal with.

Some of the characteristics of topics that work well include:

  • what you’re passionate about,
  • and is challenging and of interest to the executive,
  • that doesn’t have clear solutions,
  • with an interesting angle / insight / hypothesis that you’re willing to share.

By demonstrating your willingness to share your insights / hypotheses, you’re putting some personal capital on the table. When executives recognize this, they may reward your openness by sharing their own personal insights and hypothesis.

Having a Safe Conversation

Very importantly, this must be a “Safe Conversation.” What you are each sharing is to the benefit of each of you as individuals, and not to become the subject of the next day’s conversations amongst the project team, or at Microsoft. This also explains the value in having this type of conversation be 1:1.

To further cement the understanding that this is not part of the ongoing work, and is between the two of us, I arrange for the meeting to be over dinner or perhaps a social setting after work. That is, I’m not using the executive’s or my “chargeable” or business time for this discussion. I avoid meeting in the executive’s office or building. Otherwise, there is an implication that this is work associated with context of the executive’s role, and existing business relationships and contracts. Meeting at the office also introduces time pressures from the need to attend upcoming meetings. The goal is to create a level of separation between the existing client / partner relationship and a burgeoning trusted relationship / advisor connection.

Choosing Topics to Discuss

Avoid topics closely tied to the work you have in play at the client. Remove any sense of conflict with the Microsoft or client teams. Try to avoid the project teams questioning, “Why are we not invited to this meeting?” You have to use your own knowledge of who to inform before such a meeting. It is also your challenge to do so in a way that removes the potential of a “gate keeper's” intercession.

Discussions that I’ve personally had with executives in this setting include.

  • The huge gap in successfully achieving expectations in Strategy Execution,
  • The challenge, at a personal rather than enterprise level, of “in the moment” increasing team members’ willingness for adoption, dealing with the resistance of key members of their organization (whether named or not), and generally gaining a higher likelihood of sustaining a targeted change,
  • Dealing with a highly silo’d organization when addressing enterprise change,
  • The strange phenomenon of the low level of span of control that senior executives actually have. It changes once a strategic initiative is launched and in the hands of their subordinates. The next level of leaders comprise where the work gets done and where priorities and personal agendas get balanced,
  • In the case of a CFO, the under-utilized nature of their experience and company insight in setting and carrying out enterprise strategy. The role of a CFO in Strategy Execution has been narrowly defined over the years around financial and prioritization decisions. CFOs know that they have a lot more to contribute, but are hesitant, unsure of when and how to inject insights, within the dynamics of their peers’ span of control,
  • The challenges of balancing focus and investment in innovation, along with business as usual.

I let executives know our meeting is meant to provide an opportunity to share insights and the opportunity for me to share with them information about what some of their peers in other industries have done when facing similar challenges. When discussing lessons learned (successes and equally important for lessons learned, failures), the executive can look at ways to apply ideas to their own situation and industry.

Tips for Quickly Engaging with Executives

  1. Take advantage of small windows of opportunity with business leaders – while grabbing coffee, or during a break in a meeting, or when you run into each other in the hallway. Try to have the discussion outside of the leader’s office – try to engage on a personal level outside the role the leader plays while in the office. Talk to the person, not the role. Have a one-on-one conversation, though be willing to do follow-up with other people indicated by the business leader.
  2. Set up or find a safe conversational scenario, where you’re being direct, putting personal capital out there, and being a little provocative to inspire business leaders to share their thoughts about the topics you’re discussing.
  3. I liken the approach to these conversations as though I’m talking to my cousin about some big problem that we both have. In this case, it’s something that has been brought into particular focus in the industry where we’re working, and it would be useful to share ideas.
  4. Choose a topic that is not in the area for which you’re engaged – avoid having team members feel that they should also be involved – the topic should be of personal interest to the executive and a passion of yours.
  5. Choose a topic that has some ambiguity, and no one claiming to have “the answer.” Choose topics that present similar challenges to other business leaders, and use your research and knowledge of the ways other business leaders are thinking about the topic.
  6. Choose a challenging question – one about which you and the business leader care very strongly, but is clearly distinct from the current engagement. Use a provocative statistic or statement to spur the conversation. Be thoughtful in advance of perhaps 2-3 key potential takeaways that should be memorable from the evening. Look for the ability to land on some things that the executive can try out (or avoid!) in the near future.
  7. You don’t need to be the smartest person in the room for the topic you choose, just one of the most curious. Choose topics in which you have strong interest and passion. Share your observations about patterns that peers have identified in the same space, and suggest your interest in testing out the viability of the patterns.
  8. Use a simple provocative statistic to demonstrate the size of a problem.
  9. Listen. Give the executive the chance to be smart about the topic. Learn from their feedback, while sharing the points of view held by other peers. Encourage the executive to share insight into something that the rest of the world may not have seen. Make it a “Safe” conversation, where they feel comfortable in sharing their observations and perhaps personal challenges with the topic.
  10. Help shed light on topics, sharing your opinions and those of others without trying to convince the leader of something. Share a correlation about something you’ve noticed; suggest some tricks of the trade.
  11. Follow up and say thanks! Maintain confidences. Hopefully it was a fun, provocative evening.
  12. A final observation: In a number of cases, we’ve ended up talking for over half the evening about family, work history, hobbies, and so on, before getting down to the topic initially chosen. Could it be that that part of the conversation was the most valuable? Enjoy and be forever curious.

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Comments (2)

  1. Ed (DareDevil57) says:

    thanks for sharing.

  2. Anonymous says:

    A number of change management tools and models are not only useful when transforming a business or landing

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