Your aggressive deadlines are causing more harm than good.
I had a unique consulting client late last year.
It was a small business, biotech but a bit outside of my usual startup clientele. But the project was a fascinating hybrid of business and productivity. My work with this company was to help figure out goals and strategies to move the business forward. But also, to help this small team figure out how to better execute on the strategies we put in place. Instead of reacting to each email or phone call they receive all day, without actually moving the business forward.
Plus, the CEO was a woman, which is not as common in my industry as I’d like.
I was very excited about the opportunity.
Early in the engagement, we had a big strategy session. I do these on the early side, so that when we get to the nitty gritty, we have some sort of big picture map. After that session, we break down all the tasks and create some priorities. Work that is important for the business, not just urgent or shiny. Things to get done that will truly move the business forward.
The CEO of this small business was also in charge of writing a major grant for the company. They had a good chance of getting this grant, once submitted. And the grant would be transformative for the company.
The strategy session highlighted how important the grant was. She saw that completing it should be in her Top 3 priorities.
The following week, we sat down one-on-one to break down all the tasks involved in her key priorities. I talked to her about the work remaining on the grant. We broke it down into specific, discrete tasks. There was a lot to be done. But I felt we had made real progress in defining what, exactly, were the remaining steps.
The we talked about scheduling. About how much she already had on her plate. About her controller, about to go on maternity leave and the fact that she did not have someone to cover for her. And about the other two priorities in her Top 3, which both needed a significant time commitment as well.
And then she told me that she would be able to finish the work on the grant in the next week.
She had been working on the grant for some time. And it was quite important. But, a week? Knowing that she is still the CEO of the business. And that brings with it some day-to-day functions that are unavoidable. Plus, it’s a small team. Which means that there are always projects that are lead by other members but need her attention too.
She was insistent. One week. She could do it. She had the time. She could focus.
Because it was early in my engagement with the company, I said OK. I think some lessons need to be learned through action. They can’t be learned because someone tells them to you.
A few days passed. I checked in with the team, via our Slack channel. And I got silence.
So I followed up. The CEO mentioned some surprises that came up during the week, how she had more to do than she expected. So she didn’t complete the work on the grant. She couldn’t even tell me she had completed one specific task. The email had a deflated air about it.
I wish I could say I was surprised, or had never seen this before.
But I have seen this a lot. I know exactly what happens. And it has nothing to do with the CEO, or her ability to do the work. She is motivated and good at her job.
She just set her deadline expectations sky high. She reached for the perfect deadline — everything, all at once. And then felt like a failure because she didn’t reach it.
In all honesty, it wasn’t her, or the project, or her ability to complete tasks.
It was the deadline she set for herself.
Perfectionism, optimism, planning fallacy (the almost global phenomenon whereby people underestimate the time it will take to complete a future task, despite knowledge that previous tasks have generally taken longer than planned.). There are many reasons that people set deadlines that they can’t reach.
And here’s my plea, my wish, my hope: STOP DOING THAT.
Yes, there is an art to deadlines. It’s not a perfect system. If you drag a deadline out for too long, you risk losing momentum on an important project. Nobody wants that. But with all the small companies and startups I’ve seen over the years. And frankly, the larger public companies that I saw during my time on Wall Street. I almost never saw a deadline that was too late.
Occasionally, I’d see what we used to call an “upside surprise.” When someone hit a goal or a financial number before the deadline they had imposed. And we could argue that a company “sandbagged” the deadline. That they purposely underpromised so that they could overdeliver. (Sorry, that’s a lot of Wall Street jargon). Nonetheless, the stock market, investors, analysts always met the upside surprise with joy, every time. And so did every CEO or senior person within the company.
Which brings me back to my point. Stop creating deadlines that are so aggressive that you’ll never hit them. They are not productive. They are not helpful. And they won’t get you to your goal any faster. If anything, they delay your goal. Because you start to feel disappointment and doubt. In yourself, or in your team. Feelings that you then need to manage and work through. Feelings that can then create procrastination. Because, who wants to work on a project that makes them feel bad? That they don’t believe they can complete? Those feelings become avoidance. And the work goes even farther past the deadline.
But the truth is, these situations are not about your ability, or the ability of your team. It’s about setting concrete, realistic timelines to execute your tasks.
What are you working on, right now? Or, what are you supposed to be working on as you read this? What is the one, next thing you need to do? How long will it take? And when, realistically, can you do that this week? Look at your calendar. Think about your committments. Your travel. Your family. You might be disappointed to realize that it could be three days from now before you can get to it. That’s OK. That’s real life. It’s better to complete one task three days from now and actually do it. Than hope to do 3x as much today and fail to do any of it. Because the small, realistic steps will actually move you forward. The optimistic but missed deadlines won’t.
By the end of the engagement, I’d say that I had partial success in teaching the team to create realistic deadlines. They were still pretty optimistic. I find that most entrepreneurs are. But they had scaled their grand expectations back enough to make real, tangible progress on their business. More progress than they had made in the previous 2 years. And that was incredibly rewarding. For me, and for the team. Progress not perfection was achieved. As the old proverb goes:
A good plan today is better than a perfect plan tomorrow.