Who Asks the Hard Question When You Decide Everything Alone?

It is past midnight and the quote is open on your screen. You are the only one who has read it. There is nobody to ask, so you either press send or leave it in drafts and decide tomorrow. When you decide most things alone, the big ones look just like the small ones. Nobody says wait. Nobody asks the question, and not because the answer is hard. It is because you cannot see the question from where you are standing. I run Northlight Advisory Services, and I came to it from running operations inside organizations, so I have been on both sides of a decision like this.

What question is missing when you price a quote alone?

I once priced a job to build a website. I completed the RFP and wrote the statement of work with everything listed in detail, and we agreed. I built the website, which was meant for an event.

Things went sideways with the event planning team, and I was asked to step in to fix it. That meant effectively planning the entire conference. We had agreed on a price for building a website. I was paid that same amount.

I probably worked 40 hours a week for six months. I should have either said no, or said yes at a different rate. I have made the underpriced-quote mistake myself, and I learned from it.

Looking back, the question I needed was a plain one: is this still the job we agreed to? Nobody asked it, including me. And when the answer is no, you ask to have the contract change, or you say, okay, that means I can’t do Y and Z. It can be as simple as: my understanding was you wanted X, and this has now become X, Y and Z. We need to renegotiate. There is something okay about doing that. I had to learn it the hard way.

Scope changes are common. The Project Management Institute found in its 2018 Pulse of the Profession that 52% of projects had scope creep or uncontrolled changes, up from 43% five years earlier. That is about organizational projects, not one-person quotes, but it shows how normal the problem is.

One way to catch it earlier is a premortem. Gary Klein described it in Harvard Business Review in 2007: the team assumes the project has just failed and lists the reasons why. He argues that projects fail partly because people hold back their doubts, and that the exercise gives them permission to say them. You can run a small version on a quote with someone you trust. Where did this go wrong?

If you are the one hiring, the same point holds from your side. Agree time and scope before the work starts, and agree what happens when either one changes.

What question is missing when you keep putting a decision off?

We invested a great deal of time and energy in building a product. We thought we were ready to launch. Then we found a whole list of problems we had to fix. I was glad we found them, but it delayed things.

We had planned to use one billing tool. It turned out to be a horrible tool to use, so we moved to another. A service provider turned down my company. I appealed, and the appeal came back no. I did have another option. But then nothing happened. Not because there was nothing to do. I did not want to make the decision.

I had lost confidence in the product, in the process and, if I am honest, in myself. In the end I decided not to make it publicly available, and that decision came long after it should have. I think it was a month or two where I deferred it. I became my own bottleneck.

Did waiting help anything? No. Do I feel better now that I have decided? Yes. Did I carry that extra weight for far too long? Also yes. Those were real costs. There were nights I was working until the small hours, and I wished I had someone to have a conversation with, or someone to tell me not to be working then.

That is the question I was missing. I had an option, and I was not taking it, and I could not say why. Psychologist Christopher Anderson’s 2003 review in Psychological Bulletin names choice deferral as one of four ways people avoid decisions. It finds anticipated regret and difficulty choosing among the factors behind them. Said out loud to another person, those are easier to name.

Where do you find the second pair of eyes?

I would tell a founder to build a group of trusted people around them, so they lead out of a team instead of alone. A team forces conversations to happen. If they are the right people, they are not just saying yes because you said you wanted to do something. They think it through.

You are not unusual. In a 2012 survey of 100 CEOs by the consulting firm RHR International, 41% said they felt lonely in their jobs. Its chairman suggested a trusted advisor whose only agenda is the CEO’s and the company’s best interest, or a peer group.

Then say it out loud: we need to make this decision, and I am struggling with it.

What would I do first?

1. Before a quote goes out, ask someone to read it and ask three questions: Is this still the job we agreed to? What would make this go wrong? What will we do if they ask for more?
2. When the work grows, say so and renegotiate, or name what you can no longer do.
3. When a choice has been sitting for weeks, say out loud to someone you trust what is stopping you.
4. Remember that deferring does not make it easier.

If you want a second pair of eyes before the big ones, the Self-Reliant Builder page explains how I work with founders who decide alone, and you can get in touch when you are ready to talk it through.