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  • Writer's pictureMax Wenneker

The unintended consequences of a leader’s poor time management

Time management has been on my mind a lot lately. I have observed many founders and company leaders who, particularly in the face of larger shifts in the labor marketplace, are more stretched than ever. In some cases, these individuals are taking on additional responsibilities due to layoffs in their organization. In others, their companies are growing so fast that there’s simply more to do now and there aren’t yet more people to do it. Businesses tend to grow in a linear fashion over time, but the number of priorities demanding the attention of a leader tends to grow exponentially.


As I’ve reflected on the challenges these leaders are experiencing right now, I realized that their situations are actually not at all unique. In fact, as I thought more about it, almost all leaders I’ve ever worked with, regardless of their available resourcing, speed of business growth, or stage of company, have experienced this challenge. The challenge of time management may be exacerbated by resource constraints, but it is not caused by them.


Having such tremendous demands on one’s time is very taxing, and leaders frequently feel stressed about it. Some leaders react to this by just “dealing”, not necessarily considering the actual most optimal way to manage their time. Others might come up with strategies that are good at helping them manage that stress, but aren’t necessarily effective time management strategies. In those cases, what a leader might think is an effective time management strategy might turn out to be the exact opposite when looking at the impact it has on their teams. In today’s post, I review two leaders’ approaches that fall into this category: great strategies for themselves, but bad for their organizations.


Speedy delivery, bad execution


I once worked with a VP who managed hundreds of people in a fast-growing business. She bragged that she had figured out a perfect system for time management. Her day was chock full of meetings, but somehow she was still exceptionally responsive to email. She was also able to review her team’s work within hours, whereas other peers of hers took days to do so or simply didn’t get to it at all unless they were actively pestered by someone. And it wasn’t just brash confidence on her part or a lone observation on mine. She was well-known throughout the organization for her speed of response and delivery. She was also considered one of the best leaders to work for.


I spent some time observing this leader over the course of my work with her company, and at first I was really impressed. She attended all the meetings on her calendar. She didn’t seem to be waking up at some crazy hour to do work before the meetings started. She also managed to get in a workout most days, go out to dinner frequently, and have some downtime in the evenings. But over time I started to figure out how this all was actually happening. Unfortunately, the answer was not that she had re-invented the device that stopped time from the 2002 classic movie Clockstoppers.


When I first started working with her, she had been in her organization a long time. There was a tremendous difference between the amount of knowledge that she had and the amount that I had. This leader’s input in meetings at first came across to me as succinct and well-informed. But as I gained knowledge parity with this leader, I slowly realized that what she was saying in these meetings was, in fact, often not very insightful at all, or it was just parroting a tidbit she’d heard in another meeting. Most of her team didn’t notice it. She was a great people manager, well-liked as a person, and naturally intelligent. But I started to observe a big difference between the company’s perception of her and what I was actually hearing from her in meetings where important topics were being discussed. What she said sometimes made me think she wasn’t even paying attention.


Turns out, that was exactly what was happening. This leader was paying almost no attention in most of the meetings she attended. While she was technically in attendance at the meetings on his calendar, most of the time she was on her computer, responding to emails and reviewing work she’d been sent by her team. Her attention was divided, and she was mostly getting by on her innate intelligence and people’s positive perception of her. And this wasn’t even some sort of underhanded gambit. She freely admitted to doing this. She was, in fact, proud of how efficient she was with her time. Her approach wasn’t necessarily resulting in terrible decisions being made, but it was causing a number of problems that probably had greater cost than she realized.


Decisions had to be re-made multiple times

As I worked with this leader, I observed one pattern repeat itself frequently: her team would set up a meeting with her where they would present her with a project plan. She would give his approval for that plan (while also being on her computer and not paying full attention). Some time later, the team would have a check-in with her to tell her about the progress they were making on the project. In that meeting, she would bring up a question like “did you check with this potentially impacted team that they’re okay with this work?” Most of the time, the answer would be no. And she would ask the team to pause the work they were doing, go check with that stakeholder to make sure they were on board with the project, and then get back to her. Sometimes that stakeholder would be very concerned about the project’s potential impact and have a lot of notes on the approach or ask to consult with their own team before the project moved any further along. Suddenly, mid-project, the team would end up at a complete standstill.


A team being at a standstill mid-project is both bad for morale and a waste of resources. And this type of standstill was happening all the time in this leader’s org. Her team wouldn’t hold it against him; they were usually frustrated with the stakeholder for not being more onboard. But it was actually this leader who was causing the entire problem. By not paying full attention in the first meeting, she would neglect to ensure the team asked a key stakeholder for input. And then when it suddenly came to mind in a later meeting, it was too late. The work had already begun and had to be stopped. The stakeholder would be upset that the work had started without their input being sought. The team would be upset that this stakeholder was putting the brakes on something they were already doing. And yet it was this leader who was causing the entire problem by not fully paying attention.


The work slowly dissociated from the strategy

The other problem with this leader’s approach to time management was that her team’s day-to-day priorities were never fully vetted. The team would have a meeting with her to review their progress on their OKRs for the quarter. This leader might quickly look at the headline number at the beginning of the meeting, but then would become so engrossed in her other work that she failed to pay attention to the actual project work being done to deliver on those OKRs. Without his more strategic input, the team’s actual projects would often end up very tactically focused on one small problem (as tends to happen in more junior levels of an organization), rather than trying to address the actual problem the org needed to be focused on. The team ended up spending a lot of time on projects that delivered very little value. While the organization’s OKRs were usually achieved anyway (simply because the business was a good one), so much potential for meaningful impact was squandered because of this leader’s decision to not pay full attention. This leader truly believed she was being efficient with her time (which technically was correct), but the approach was causing tremendous inefficiency in the use of the rest of his organization’s time.


Whack-a-moling


I recently worked with another leader who also believed that he was a fantastic manager of his time. He had a very particular philosophy of time management where he dedicated 30% of his time to whatever the company’s biggest problem was at the moment. Regardless of his other priorities, he would consistently devote that 30% of her time to the issue that he believed was most pressing for the business. In his mind, this was a way to marshal more resources and give more support to whatever most needed it.


When he first explained this approach to me, I thought it made a lot of sense. It stood to reason that the most important things in the business should be getting resources and attention. When user growth stagnated and became a problem for the business, he set up an ad-hoc meeting with the leaders from all the departments that could impact this problem, and asked for a brainstorm on what could be done. He organized a list of action items that he then assigned out to his leaders as well as himself, and set a check-in for a few days later to review progress. This approach seemed really productive. He was getting the right people involved and getting resources focused on the right problems.


Over time, I watched his approach play out across nearly every part of the organization. For a few weeks, user growth would be the biggest problem. Then it would be client onboarding. Then it would be marketplace efficiency. After awhile, as is natural in any business, some of the top problems would start to repeat themselves. After a couple months of not focusing on user growth, this leader at some point determined that, once again, user growth was becoming an issue. So he went through the same steps she did the first time. And that’s when I realized how problematic this approach actually was.


Bad tactical decisions were being made because a senior leader shouldn’t have been making them

The next time that user growth was this leader’s focus area, his meeting on what to do about it went very differently than the first one. The first discussion yielded a number of great ideas. The second one, only a couple months later, did not. The team was already working on all the things they thought needed to be done in order to fix the user growth problem. Most of the items that were discussed in the first meeting were things that would take time to see results. But this leader continued down the same path he had before of asking people for more immediately-executable ideas to solve the problem. Only this time, since the experts in the area didn’t know what else they could do, he made the list for them. Over the objections of a number of marketing team members who, with a deeper understanding of user growth than he had, did not believe the leader’s ideas made much sense, he assigned out his list of tasks and, like last time, scheduled a check-in for a few days later to see how they were going.


A few days later, nothing had changed. He asked for more ideas. None were forthcoming. Now he began to blame the marketing team for not being creative enough, or for attributing external factors when the problem (in his opinion) was fully in the team’s control. The team left the meeting looking very defeated.


A couple weeks later, I watched the same series of events play out with another team when this leader decided that their area of focus was the company’s biggest problem and required his attention. Another meeting, more pushback followed by assignment of bad ideas, and then no progress. And the cycle continued to repeat itself with every other team. No improvement was being made in these problem areas, so the leader kept doubling down his efforts to try to coax progress, with the ultimate result being the same, though each time with more frustration from his and from the team working on the problem.


I checked in with some of the managers whose teams had recently been this leader’s focus area and who had experienced this cycle multiple times. All of these managers expressed the same frustration. This leader was telling their teams what to do, but he was doing so without nearly enough understanding of the function. The team was doing what they were told by this leader because they ultimately reported to him, but they knew these actions would not produce the desired results.


Employees worried they would end up in the spotlight at any moment, morale plummeted, and productive discussion dried up

The other frustration these managers expressed was that this leader was putting their teams on edge. Over time, employees watched this same cycle play out where this leader decided to, somewhat at random in their minds, dedicate his time to a problem in their area. This led the team to feel like they were at risk of being in the spotlight at any moment, and the spotlight was not a fun place to be with this leader. The way he was focusing on the problems, these employees felt as though they needed to defend their actions and explain why they were doing what they were doing. Instead of feeling comfortable using their expertise to try things (and sometimes fail), they were just doing exactly what they were told by this leader. Morale became extremely low in a team whenever they were in this leader’s spotlight. And when they weren’t, there became a constant fear of being in it at any moment.


The company’s resources were being constantly reallocated to bringing up the rear

This leader was definitely bringing attention and resources to bear on the problem he focused on. But the issue with his approach was that he was dedicating herself and his company to the areas that were performing the worst. Basic management principles state that a manager’s time should be spent on maximizing performance. Instead, he was constantly focusing his time on bringing up the rear. It was as if a coach were spending all their time working with the worst player on the team to help them become average, while the better players with far more potential were getting ignored. The result was that the leader’s focus would stay with a team just until their metrics improved enough to make that problem no longer the biggest one. The best-performing areas of the business got none of his attention until they stopped being the best-performing. Company employees experienced significantly whiplash, and forward progress in the business became very difficult to achieve.


Takeaways from these leaders’ time management philosophies


As the stories of these two leaders demonstrate, determining whether a time management strategy is an effective one as a leader should be done based on outputs, not inputs. It is also important to identify and consider the unintended consequences of your time management strategy. While these two leaders were incredibly confident in their individual approaches, both were viewing their effectiveness myopically, not seeing the results beyond themselves. Neither understood the impact that they were having on others.


In my experience, there are a few key things to consider when determining your own time allocation as a leader:


Is your attention focused?

Company leaders tend to have the busiest calendars. In order to keep up with their work, most of them multi-task. As was the case in the first example, multitasking can lead to critical information loss. It won’t be obvious at first, but it will degrade the effectiveness of your organization over time. The best thing you can do for your company as a leader is be fully present.


Is your approach validated by your direct reports?

It doesn’t matter how much confidence you have in how to manage your time if you don’t have the buy-in of the people around you. Your effectiveness as a leader is determined in large part by your ability to hire, enable, and retain your best talent. Make sure they agree with how you manage your professional priorities.


Are you a blocker or an enabler?

Leaders, particularly in a startup setting, tend to be doers by nature. To some extent, that is necessary. In a startup of 10 people, even the CEO should be getting their hands dirty. But if you’re doing too much, you may not be allocating enough time for supporting or enabling. Many leaders are so busy that their teams often end up stuck waiting for them to be available to approve their work or complete a necessary step in the process. If you’re often a blocker, delegate more.


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