BL&T No. 189: Weighing Upfront Investments in Potential Client Engagements

Agency Leadership

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is sent weekly on Mondays. In every edition, I share lessons learned in agency leadership, life, and e-commerce. This post does not include all the details shared in the newsletter sent via email. Subscribe here.


"And then it dawned on me. I was a salesman. Dick was just a consultant. He didn't do any selling at all. Instead, he just went in there and started helping them."

From "Getting Naked" by Patrick M. Lencioni [Book]


A team member recently asked me if we might be spending too much time on the new business process for a potential client. For context, the client is merging two brands with sizeable e-commerce websites and migrating them to Shopify Plus. They're new to Shopify, so we've held several follow-up meetings and workshops to bridge the knowledge gaps and work toward locking in a project approach.

I took this team member's question as an opportunity to align on the value of these initial investments in building lasting client relationships.

Here’s my perspective:

Not every prospect warrants the same depth of research and discovery. However, once we decide to take an initial call, we're fully engaged—we don't shy away from asking questions to uncover as much as possible and offer strategic recommendations.

From there, it's about understanding if:

  1. We can help the client achieve their goals.
  2. We have enough information to create a proposal.
  3. The budget and timeline align with the project's complexity.

If all of these check out, we evaluate our likelihood of winning the project, considering things like the warmth of the lead source, how well we can demonstrate relevant competency, and the number of other agencies in the running. We'll then decide if it's worth pursuing and which steps are necessary to narrow in on a project approach and proposal.

When we take a path similar to the client mentioned above, I view it as an opportunity to give both teams a sense of how we might work together. In this case, the client has in-house resources that will be critical throughout the engagement. Getting folks like this in the room from the start to work through requirements and get a feel for their working style has been invaluable.

If all goes well, it’s as though the project has already kicked off, even though we haven’t yet defined the scope. At this stage, it’s about ironing out the details, signing the necessary documents, and moving forward with the work.

On the flip side, it could all fall apart, and... we lose. But do we?

Not necessarily.

Sure, it never feels good to lose an opportunity, especially after investing time and resources, but we never regret putting in the time to develop relationships and add value. You never know when you might leave a lasting impression that opens doors to opportunities that may not have been available otherwise. For instance, last year, we put considerable effort into a proposal for a desirable client. We didn’t win the project, but the impression we left was strong enough that when an executive stakeholder from their team started a new venture, they remembered us and brought us on board.

So, are we giving too much?

I don't think so. I believe putting our best foot forward from the start, whatever that means for the situation, is the only way to go, no matter the immediate outcome. At best, it's the cost of winning the opportunity. At worst, it's an investment in the future, nurturing relationships that might one day evolve into fruitful partnerships.


When has my upfront investment in a new business opportunity paid off in unexpected ways?

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