You’re back at it. You’ve gotten up with your alarm, had your breakfast and your morning walk, and sat down at the computer with your fresh cup of coffee. Instead of the green light you’ve been working for months to secure from a funder, an investor, a client, you’re staring down a tunnel of uncertainty with no visible light at the end. Your coffee is now cold and hardly the pick-me-up you need. In moments like this, a hint of reassurance that you’re on the right path would be helpful. But you’re probably alone in your home office or the leader of a team that is looking to you for that reassurance.
Listen to the signals
When I find myself in these moments or am coaching clients through the long haul that is building, I think about the incubator I built for a venture capital client. The incubator matched high-potential startups with expertise and mentors from the fund’s network. We kept meeting promising, well-aligned startups, but they were often missing one thing we needed to see in due diligence. We wanted to use the fund’s network to help strengthen them as investments.
There was no set time limit to be in the incubator. I had a quarterly check-in cadence with the companies, and if I felt they were making progress, I kept them in the program. At a demo day, I met a deep tech software company that was interesting and well aligned with the fund’s thesis. The investment committee was excited about the potential of their customer base and their technical expertise, but the company was based in Europe, and we weren’t sure whether they could grow to venture scale in the US. We also had some concerns about execution risk. They had built the company, but were they the team to scale it? Anchoring on their existing traction and potential, I matched them with a mentor in the fund’s network and put them in the incubator cadence.
At every check-in I looked for a few specific things. Were they landing paid pilots with US companies? Did the team know where they were weak, and did they either improve or bring in someone who could support them? When we and the mentor gave feedback, did they act on it? I started to feel uncertain about this relationship because no other engagement in the incubator had looked quite like it. I kept the cadence and trusted what I could measure, and each milestone settled a little more of the investment committee’s concerns. The company eventually hired the mentor we introduced them to, which indicated the match was working. After nearly two years, the fund invested. They were the final investment from the first fund, and the incubator program proved successful, surfacing 19% of that fund’s investments.
Measure incremental success and recognize the small wins
I couldn’t have predicted that we would actually fund that startup when I first put them in the incubator program. However, I could tell you whether the pilots were growing and whether the team was acting on feedback, and that was enough to keep engaging with them. Most of the founders and nonprofit leaders I work with are in a similar stretch, working diligently towards a goal but without any indicators to know they’re on the right track. They compare themselves to their peers who’ve raised a Series A or landed that big, recurring funder and wonder when their turn will come. But we only see the LinkedIn announcement of these wins, not the months or even years of effort and rejection that preceded them. Building is iterative. A big goal can stay out of reach for a long time. In the meantime, smaller signals can tell you whether to keep going or change course. They also give you something to point to on the days the big goal feels elusive.
Whether you’re building a program, setting a fundraising goal, or working toward a revenue number, keep the final goal in view and define the steps that show you’re headed there. What are the few specific, measurable things you need to see to feel confident? Monitor these metrics at regular intervals and ask yourself whether they are building momentum in the right direction.
A current nonprofit client of mine is feeling the familiar discouragement of not having raised their target for unrestricted funding. Meanwhile, the fundraising process is clearer and more consistent, relationships with funders are moving forward, and introductions and intentional networking are bringing in new connections. While none of these signals are the big gift we are working toward, they tell us we are moving in the right direction.
As a fractional COO, I help leaders set the goals, KPIs, and operating rhythm, so they can see where they stand and celebrate milestones on the way. This month, write down one thing you need to see to know you’re on track toward your larger goal, and put a check-in on your calendar. If you’d like help naming that milestone, book a 30-minute call here and we’ll figure it out together.