Deadlines are Lifelines

A lot of leaders that I coach or talk to (I do just talk to people sometimes) bemoan all they need to get done. There’s the typical litany of executive director duties – dealing with cash flow, preparing for board meetings, getting the team in sync, approving the invite for the gala. And there’s the fire drills and interruptions – the last-minute signature request, sign-off on the email solicitation that is behind schedule, the picking of your brain on some stray topic.

We ricochet between large organization-wide issues and urgent (although rarely of great importance) to-dos. The first few rebounds are manageable, but ultimately, we come away nauseous, stiff-necked, and praying for it all to just be over.

Amid all this pressure, perhaps ironically, the pathway to greater calm and stability is the addition, not subtraction, of deadlines. Meaningful deadlines.

That might seem absurd and impossible, since people are banging on your door (or Slacking, texting, and emailing you) incessantly. They are throwing the deadlines at you, aren’t they?

Yes and no. Those little tasks are fire drills, not goals. They are immediate dopamine hits – I finished something! I’m a good person! – but also distractions.

Let’s be honest with one another here in the safe space of this post. Amidst all the task completion and dopamine hits, there is a whole lot of procrastination going on. Do you really need to sign that check request, respond to that question about something coming up in six months, or Google the etymology of the word “histrionics” right this second?

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Deadlines aren’t that. They are possible points of closure – intermediate successes – during larger projects or strategic initiatives, the important stuff we always want to focus on more but bemoan – see paragraph #1 – not having time for.

We’re swatting at the minutiae like a game of whack-a-mole rather than chipping away at larger – more overwhelming in their immensity or distastefulness – tasks that are stepping stones along a much longer journey.

Unfortunately, the larger string of related tasks – and the goal they lead to – looms large. Even when we think we’ve put it off, we haven’t.

Enter the Zeigarnik Effect. Unfinished tasks – open loops in our mind – are easier to remember than the ones we completed. They simmer there, creating a stew of cognitive unease.

That email you answered, thank you letter you signed, and LinkedIn feed you perused did not get you a step further on your strategic plan, annual budget adoption, or morale improvement initiative. And they didn’t even help you forget about them. What good are they, really?

You can’t forget the big stuff but forget the small stuff you did almost immediately.

See why I love a good deadline? I love them for the structure and focus they provide and – done right – the procrastination they help to obliterate. They are the antidote to the malaise of Parkinson’s Law (work expands to fill the time you have set aside for it). By shortening the amount of time we allot to get something done, we sidestep the minefield of procrastination.

These small points of completion also help us to iterate and improve throughout a process. We can’t cram for our strategic plan goals or whip out a thoughtful budget the night before the finance committee meeting. We need timelines that meet the demands of the project and deadlines to keep us moving forward.

Making it Work for You and Your Organization

One of the many challenges of leadership is that you need to make deadlines work for you (first) and then your team (and organization and board of directors, if you are the executive director).

Leadership is a symbolic game. Your team takes its cues on how to manage timelines and priorities (and everything else) from you. They won’t understand that you are the leader and have different demands – they will understand that you are modeling behavior you deem acceptable – hopping from lily pad to lily pad rather than focusing concentrated effort on important matters.

To make deadlines work to your advantage and be the shining example of focus you want to be:

• Timeline as Much as Possible. Make sure the multiple steps of a repetitive project (like preparing for a board meeting) are mapped out clearly and shared with everyone who contributes to its success. These routines establish a way of working that translates well to bigger projects and longer initiatives.

• Add Open Space to Calendar. One thing is certain. Every day there will be small tasks that pop up and need your attention. Your choice is to deal with them all at the same time or to have them interrupt the flow of the bigger projects you are working on. I recommend letting people know that you deal with requests of this type either (1) for 30 minutes in the morning and 30 minutes at the end of the day, or (2) in a one-hour block of your choosing. The only reason to interrupt you outside those times is for something that is truly urgent.

• Cap the Number of Email Exchanges. If an issue takes more than two emails, either pick up the phone to discuss it or schedule 15 minutes on your calendar to resolve the issue quickly. Unanswered emails haunt you. Exorcise them.

• Time Block and Mean It.  Many workers block off one or two hours on their calendars for larger project-based work. Unfortunately, they find it hard to honor that block of time. Set Slack to unavailable; close your email, browser, and everything except the task at hand. And put your phone in a desk drawer or another room, turned off or silent.

• Build Your Stamina. If two hours of uninterrupted time without your phone is too frightening to face, start slowly. Set aside 30-minute blocks and increase them each week until you are at a substantial amount of time and have the mental fortitude to avoid distractions.

How to help the team

Some of the habits that help you will also help your team (like limiting the number of email exchanges before moving to a faster form of communication). You can strengthen everyone further through some tried and true practices:

• Make Deadlines Visible. Post deadlines where you and your team can easily see them – a shared calendar, project management tool like Asana or Monday.com, or a whiteboard (if you dare to work in person). Visibility creates accountability.

• Review Timelines During Meetings. Use your leadership to help your team be accountable for their deadlines. Begin by establishing deadlines that are assertive (not unachievable) and then review progress during team meetings. As timelines collide, you can help adjust priorities in line with your organizational strategy.

• Break Big Projects into Smaller Goals with Intermediate Deadlines. Deadlines can be the small wins of bigger change initiatives or projects. Each deadline that we meet is proof that we are a bit closer than we were a day, month, or week ago. When the team meets an important deadline, celebrate (donuts, popcorn, or crudite can work wonders).

• Use Work Blocks Organization-Wide. If time blocking works for you, just imagine what it could do across the organization. Setting a common time that the entire team agrees to work on bigger initiatives without interrupting one another can increase productivity.

Setting and working toward a deadline does not have to mean frenzied time crunches and failed attempts at perfection. They can help communicate purpose and priority while setting a tone of continual improvement – progress not pressure to be perfect.

Please don’t go from constant interruptions and aimless procrastination to Type A rigidity.

A deadline that has been met is proof that we are accomplishing what we promised to ourselves and our communities. Whether it is preparing for our next board meeting, sending out an annual report, or finalizing the next program evaluation, deadlines are gifts.

If you want to develop a practice of setting lifeline-yielding deadlines, let me know. I’m here to help. You can email me at gary@garybagley.com or DM me on LinkedIn.