Not Every GTM Story Is a Success Story

Most of what people read from me in my articles and social media is about what worked - a channel that landed, a positioning shift that clicked, an audit that uncovered something fixable. But I've had my share of engagements that didn't go anywhere, and I think those are worth talking about too.

Whether I can actually help a company with GTM is usually obvious within the first month. Not because I'm particularly sharp about it, but because the signals show up fast - the market fit isn't there yet, the product isn't ready for the motion they want to run, or the gap is somewhere GTM can't reach, like the product itself, the team, or the funding runway. A month is normally enough to see which of those it is.

The most diligent thing I can do at that point is be completely honest, right away. Not soften it, not string the engagement along, not wait for a more comfortable moment. I explain my reasoning - what I'm seeing and why I don't think I'm the right fit to move the needle - and I suggest what I think the company actually needs, even if that's not me.

Sometimes the company hears that and asks me to try anyway. When that happens, I give it everything I've got. I don't go through the motions just to prove a point I already made. But I also try not to let a disappointing result get to me too much, because I called the odds honestly upfront, and the outcome doesn't retroactively make that assessment wrong.

Other times, the company hears me out and agrees. That's usually where we part ways, right there in that conversation, and honestly, that's fine. It's the honest ending to a conversation that started honestly.

And every so often, I'm the one who has to push for that ending. If I strongly believe there's nothing I can do to move things forward, insisting on parting ways is sometimes the better call, even if the company wants to keep going. Continuing something you don't believe in doesn't fix the underlying problem - it just delays everyone finding that out.

Money comes and goes. Being honest and straightforward, even when it costs me an engagement, is what keeps my conscience clear and lets me sleep at night without any remorse. Your Jiminy Cricket should always be proud of you.