Partnership Design: The Importance of Listening and Asking Questions

Long before I founded Point Road Studios, I was designing partnerships. Building relationships has been the common thread throughout my professional career – whether as a teacher in Germany, a Communications Director at a start-up non-profit, or an account and sales executive. In my experience, a strong foundation of mutual respect and trust is key to whatever partnership you are forging.

The first step to building meaningful, long-lasting client engagements is listening. Listening, listening, listening. Yes, I will share anything a potential client wants to know about me and the work I do, but my focus isn’t on telling my own story. I want to understand your story. I am incredibly curious to learn who you are, the kind of work you do, and what the catalyst was for you reaching out. (I’m proud that 4 years into running my business, all of our work has come from inbound interest.)

My focus isn’t on telling my own story.

I want to understand your story.

In the early stages of dialogue with a prospective client, we shape a shared understanding of who we each are and whether we have a potential fit for partnership. If the fit feels off, it is still my intention that we each leave the conversation having learned something. Life is too short to feel like you are “wasting your time” and I’m a believer that every interaction – regardless of outcome – offers the chance to learn and grow together. If the fit feels right, we move into designing our work together. This whole time listening never falls out of focus. Listening is the single most powerful tool not just in the process of designing an engagement, but in creating real, positive impact. And that’s the stuff I’m after.

As we move into the process of co-creating a partnership, there are five, simple questions that I use to guide the design of my engagements. Nothing fancy or complicated. It starts with these four: Who? What? If/then? And how?

The people and organizations I have the privilege to serve aren’t cookie cutter and I don’t believe the solutions we craft should be either. As a designer and a coach, I’m looking for a clear understanding of the opportunity to serve. The better I understand where my client is at the beginning of an engagement, the better able I am to guide them toward a solution that both meets them where they are and pushes them to grow to where they want to be. My design conversations rarely look identical in their flow, but the who-what-if/then-how framework allows us to move with intention through the conversation. Holding the client’s overarching objectives in mind, we dive in.


I often begin my exploration with an understanding of the people involved. Sometimes an individual reaches out who is looking for help for him or herself. When that is the case, I have the fun task of getting to know this person and understanding what prompted them to be in touch. For those clients who are part of a larger organization, there is usually more digging to be done. I might ask: Who do you want to support through this engagement? Or: Who is the target audience? Perhaps the CEO of a mid-sized firm wants to focus on her relatively green management team. There might be an HR leader looking to build an executive development program for the firm’s rising women leaders. Sometimes there is a team or group that has been identified as critical for a cross-functional initiative.

The who really helps to ground the engagement in a personal, human way. And my clients tend to feel more grounded in how to think about what those specific people need. Sometimes, especially in a larger organization, a client may have an idea about a general group he’d like to bolster (e.g. emerging leaders, frontline managers, senior leadership), but not necessarily know which specific people will participate in the program – at least to start. Other times, a client might not have any idea about who needs help, they just know that they have a problem that needs solving and they need guidance in figuring out how to circumnavigate it. All of these uncertainties are just fine in this early design stage. What I want to do when it comes to “The Who” is get clear on what is known, what isn’t known and keep moving.


As I hold my understanding of where a potential client needs help, I’m asking questions like: What is the learning that will be impactful for this person or group? The what is really all about content – about the ideas that, once shared, will move a client toward the desired shift. In coaching this is usually about an overarching coaching objective, like, for example, “a focus on time management for the sake of scaling leadership scope and effectiveness.” For a development program, this might center on something more broad like “developing the next generation of leaders” or something more specific like “management 101 skill development with a particular focus on managing resources – time, people, and finances.”


If/then brings us back to the overall purpose for the engagement. I might ask: If we have a wildly successfully partnership together, then what will be different at the end of our engagement? This primary if/then question doesn’t run to the solution in the way that the what question sometimes can. This is where we can lift back up to the bigger elevation of our objectives and check in on the outcomes a client is hoping to achieve. This is also a great space for us to test out any hypotheses we may be formulating. If we offer ____ service, with ____ focus, to ____ person/people, then will we get the desired result? This if/then line of inquiry makes sure that we are squarely focused on what matters most and that we’ve tested our hypothesis statement to ensure that – at least from where we stand today – we are building an engagement that will meet (or exceed!) the client’s needs.


I love how questions. How moves us into a space of process – of doing. How can we best accomplish the desired outcomes? For partnership design the how is all around structure. What format (how!) will best serve this person or group in driving the desired outcome? Is one-on-one coaching the right fit? For what duration? Frequency? What about skill-development programming? How long do we want the sessions to be? Virtual or in person? Is a one-day, 6-hour bootcamp the right answer, or perhaps 6 1-hour sessions spread across 3 months?

To answer the how questions, I want to understand the client’s boundaries and current circumstances. Have they been in the midst of a training program that didn’t work? And if so, why? Is this the first time they have ever offered an offsite planning retreat? Are the participants who will participate in our programming overwhelmed with meetings? Do they have a strong preference for working over video? Is it important to them to have face time?  Even as I seek to understand the client’s boundaries, I know it is likely that I am going to push them. Having designed leadership development partnerships for over a decade, I’ve learned a lot along the way about what works and what gets in the way. My goal is to meet the client where she is while also guiding her to consider other options based on my expertise.


After I bounce around with a potential client exploring the who-what-if/then-how questions, I usually have a pretty good idea for a comprehensive, multi-stage approach to how I can support a client. The benefit of being naturally forward-leaning is that it’s pretty intuitive for me to look several years out into the future. BUT – and this is a big but – the grand, comprehensive approach is not always the right starting point. And it turns out, no matter how far into the future you look, the only place we can begin our work is from where we stand today. And that takes us to question number five. My final area of inquiry for a prospective client is this: Where is the most impactful place for us to start?

Some clients really want and are ready for a multi-year, multi-constituent, multi-pronged approach. They value being able to paint a medium to long-term vision for program participants and want to make sure we’ve got an integrated and cohesive approach as we do so. And that’s awesome. Others – whether because of capacity, or budget, or simply a desire to pilot a approach before rolling it out more broadly – want to start small and see how things evolve. And guess what? That’s awesome too! The key is for us to work together to figure this piece out. And that takes us right back to where we started. Listening. And asking questions.

It doesn’t matter how many partnerships I design or how many clients I serve; each one is unique and demands individual thought and care. I am ever grateful that my clients are willing to include me as they seek ambitious objectives like growth, change, and teamwork. But no matter how many diverse approaches I craft to help steward my clients’ goals into being, some things are evergreen. I am committed to entering into every single engagement with a deep curiosity – and a strong belief that there is nothing stopping you.