Steve came to me about a boss who sets impossible deadlines. All managerial flaws aside, the person he worked for (who I’ll call Harriet) was an amazing woman. A charismatic leader, able almost single-handedly to move ideas into reality through her charm, energy, intelligence, and undying belief in her ideals.
But she also doesn’t know how to stop long enough to allow others or circumstances to catch up with her. Just when staff wrap their heads around one project and get it going, she comes to them with three new ideas. Ones they MUST get started on right away. And it was driving everyone else in the office crazy.
Working with impossible deadlines
When Steve first began working with Harriet, he was amazed by the constant rush-rush-rush toward deadlines. The place was a madhouse, day-in and day-out. There never seemed to be a time when they weren’t desperately trying to catch up with all their work while racing toward some new deadline. And too often he heard Harriet’s impassioned cry, “It’s a DISASTER!”
With all the good things one could say about Harriet — and there were many — this was definitely a glaring flaw. One that affected not only projects in progress, but also staff morale and the general workplace environment. These words usually meant Harriet didn’t think they would meet a key deadline. And so time to work even harder!
But, it also could mean Harriet hadn’t gotten the positive response she expected from someone she was trying to win over. Or it might even mean the salad bar didn’t have shrimp salad. And the frustration she felt, as unconnected as they might be to the tasks at hand, added to her need to accomplish NOW.
Harriet was indefatigable. She was driven by her passion to change the world single-handedly if need be. Steve admired her greatly, but knew that something was very wrong with the way the office was running. And he also saw that the deputy director, while a truly caring person, had no clue how to make things better. While this wasn’t exactly Steve’s job, he decided he would find a way to improve things for everyone.
Getting a handle on deadline-crazed boss
Steve did his work and did it well — even amid an atmosphere of often impossible deadlines and “rush-rush-rush” Harriet. When he first started, he watched how the place functioned and how everyone behaved, especially Harriet.
After a couple of months, he gained the trust and respect of Harriet and the rest of the staff and began his campaign to help improve the situation in his department. His observations showed two key reasons for the madness:
- Harriet single-handedly made commitments to others about new ideas and
expected her staff to implement them. - Harriet made up deadlines, pushing them well ahead of the real deadlines.
Steve decided to focus on what he could and couldn’t influence in Harriet’s behavior. He knew he couldn’t change who Harriet was or her passion, nor would he want to. But he thought he might at least help slow down some of the frenetic pace that was serving no one.
Although Harriet was a zealot to her cause, once Steve expressed an interest in helping improve outcomes and took time to explain this to Harriet (including the effect of impossible deadlines), she eventually admitted the place might need help. (That won’t always be the case with a boss, but it’s worth a try.)
Tackling impossible deadlines
So, for everyone’s sake, Steve went ahead with his plan to focus on the deadline problem. He did his research and made sure which real deadlines were not the same as the ones Harriet created. Then he took a chance and brought up the issue with Harriet, knowing that even if he didn’t get the answer he wanted, the seeds for change would be planted.
Taking a deep breath, he took the latest deadline-driven document off the overworked secretary’s desk and walked into Harriet’s office with it. Steve held it up, looked Harriet in the eyes, and strongly and sincerely said he would be happy to take full responsibility for getting it in on time.
But he also carefully explained that he had researched the true deadline, and found they still had two weeks. And again, looking her in the eyes but with a warm “no disrespect to you” smile, he suggested they needed that time for other projects that really were due right away. And could fail if full attention was not paid.
At first, Harriet wouldn’t listen getting caught up in her own mindset and “it’s a disaster” thinking. But Steve calmly continued, addressing each objection one by one, stressing this was about all her projects being successful. Whether it was his sincerity or whether Harriet finally grasped the concept of the real versus impossible deadlines, Harriet agreed.
So how did it turn out?
Steve realized that Harriet’s creative brain never stopped working. And if it had too much hands-free spare time, she’d keep giving birth to new ideas for them to work on. But if Harriet became more involved in existing projects (in a way that utilized her skills), she wouldn’t have as much free time to think of new work for everyone else.
Plus, by getting her hands into the workload, she’d see more directly how much time was needed for what was already on the table. Steve suggested concrete ways for Harriet to better focus her attention. And, though it took some time, Harriet realized she couldn’t continue committing the staff to so many new things without getting the old projects solidly in place.
With encouragement and appreciation for her efforts from Steve and other staff, Harriet finally realized how directly her actions influenced the way the office ran. And that they needed to first strengthen the programs they had before branching off into new areas. That was exactly what Steve was trying to tell her. And with patience and respect, the plan worked.
A few more thoughts
Steve handled this situation just right. After that and without too much effort, Steve was slowly able to change the way deadlines were determined in the office. He took it on as his responsibility (with all hands on deck coworker help), and the net effect was things got better for everyone.
Of course, every boss is different. And not all as ready as Harriet to participate in a way that actually helps … without making things more complicated. And some you wouldn’t want to get into the details, especially micromanagers or non-delegators. But some version of this method of addressing impossible deadlines is worth a try.
For those bosses who would not want — or YOU would not want — to pitch in, there still may be ways to approach the deadline problem. Odds are they’re also not ones to be told they’re wrong. But they might be open to getting more updates that also give them a chance to pitch in ideas. “We can’t do it” might not fly. But asking for ideas to overcome real obstacles might get you somewhere.
The best results usually come when ideas are owned by the person you’re helping. Once Steve figured out where productive changes could be made, it was easy to start planting the fertile seeds with Harriet. Hopefully, no matter what type of boss you have, there is a way to help them help you!
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