Dear Ryan,
I need to say something I haven’t said out loud yet: I think I may have just cost my firm a significant amount of money. And I’m not entirely sure how to tell anyone.
I’m a COO at a broker-dealer. Six years in the seat. I’ve navigated platform migrations, survived two regulatory audits, and managed through a global pandemic without losing a single key person. I say all of that not to brag but to establish that I am not someone who gets taken easily.
And yet here I am.
Eighteen months ago, a vendor walked in with a pitch that answered every problem we’d been struggling with for years. New account complexity across registration types. CRM sync. Orion integration. Custom dashboards. Advisor-facing intelligence tools. Every question I asked, they had an answer. Smooth, confident, demo-ready answers. When I specifically asked about one key TAMP integration, they didn’t hesitate. “We can absolutely build that.”
I didn’t just take it to my CEO. I took it to the board. I built a full business case with projected efficiency gains, headcount savings and a three-year ROI model. The budget approved was just north of $400,000. I was the most confident person in the room.
We are now ten months into implementation, and I’ve made a discovery that keeps me up at night. There is no product. What I actually bought was a custom software development project with no fixed scope, no guaranteed timeline and a vendor whose primary skill, I now understand, was selling.
I’ve made a discovery that keeps me up at night. There is no product.
There is a team of developers building something that looks like what I was shown in the demo — for us, from scratch, on our dime. Every capability that was demo-ready 18 months ago is apparently “demo-ready” in someone else’s environment. In ours it’s a change order. Every integration I was promised is a separate statement of work. The TAMP integration I specifically asked about is, I was told last week, “on the roadmap.”
I have a CEO who trusted my judgment. I have a team that’s been living in workarounds for ten months. I have a vendor who is technically not in breach of anything because I apparently signed a contract that said a lot without promising much. And I have a board presentation in six weeks.
I’m not asking how to fire the vendor. I’m not looking for sympathy. I’m asking how a COO who sold this walks back into that boardroom with any credibility left.
— In Too Deep To Pretend It’s Fine
Dear In Too Deep To Pretend It’s Fine,
Let’s name what actually happened. You didn’t get outsmarted. You got sold. There’s a difference, and it matters more than you think right now.
Snake oil works on all people. Especially on the smart ones. The pitch was engineered for someone who asks good questions. “We can absolutely build that” is a perfect answer because it sounds like a yes when it’s actually a maybe wrapped in a contract with no concrete guarantees. You asked the right questions, and you got manufactured confidence in return. That’s not a judgment failure. That’s a procurement failure. And those are survivable.
Now. The boardroom.
Don’t walk in with a recovery plan before you walk in with the truth.
Don’t walk in with a recovery plan before you walk in with the truth. The normal instinct when credibility is on the line is to bury the problem under a slide deck full of next steps.
Resist it hard. Your board doesn’t need a plan yet. They need to see that you understand exactly what happened and that you’re not just managing their perception of it.
Here’s your whole presentation: “I bought a promise instead of a product. Here’s what that cost us, here’s where we stand, and here’s how I’m thinking about what’s next.”
Three sentences. No spin. No “the vendor misrepresented.” No passive voice. Own the room by owning the decision. Then plan out the near future. Baby steps.
The leaders who survive moments like this aren’t the ones with the best recovery plans. They’re the ones who walk into hard rooms and tell the truth without flinching.
You sold it. Now go deliver something better.
The truth.
— Ryan
Ryan George is the Chief of Staff of Docupace.
