4 ways Accidental Managers can compromise startup success

Elena Dexter
8 min readMar 26, 2022

This story is a part of the ‘People’ Risks series:

  1. Intuitive, Trained and Accidental Managers
  2. 4 ways Accidental Managers can compromise startup success

As I explored in my previous post, some people end up in leadership roles unplanned. I call them Accidental Managers.

Often, decisions like the business founder taking on management work or promoting an early employee are made almost unconsciously, because they seem like quick, easy and cheap options. Ironically, taking that route can turn out to be quite costly in the long run. I have seen it happen and have to admit, been in that situation myself.

By sharing what I’ve learned, I would like to empower both business founders to make thought-through decisions that account for the risks and long-term consequences.

Let’s take a closer look at a few side effects these choices can have on early startups.

Team

When deciding to put an Accidental Manager in charge it’s worth pausing for a moment to consider whether this person is capable of making the team more productive and on target. If not, would this decision have the opposite effect?

The trickiest part comes into play when you decide to ‘just manage X for now’ or promote an early employee who might not have the skills and expertise to do the job.

What often gets overlooked is: that ‘figuring things out’ takes time, which at an early startup almost always equals burning cash. Be it money from an investor, a HELOC against your house or even the lost opportunity cost of not taking a paycheck from someone else — it is expensive to move slowly.

Things go particularly painfully if management and leadership is not full-time job for a person in charge. The learning process ‘alongside other work’ can take months or even years, and in the meantime, the team and the business have to live with the day-to-day impact.

Here are just a few examples:

  1. The team is not given what they need to do their jobs

New Accidental Managers might not know what the team’s inputs should look like and therefore might not think to take care of preparing everything required.

The missing part can be information, making sure other work is finished first or a decision to proceed a certain way. Either way, if the team doesn’t get all the pieces, they might consider themselves ‘blocked’ and can respond with no-regret YouTube watching, while waiting for ‘the company to figure things out.’

The real danger lies in not realizing that this is happening and therefore not doing anything about it. Here you have it: a manager thinks stuff is being worked on, while the team is sitting around waiting on something.

Even as an experienced manager, I still encounter situations when I check how someone is doing with a task only to be told that they ‘were not given X, therefore couldn’t start.’ My favourite part? They didn’t bother telling anyone about it… Now imagine a new Accidental Manager, who might not think to ask!

2. Tasks are given with not enough context or direction

One thing managers of all grades should remind themselves about is: that employees don’t know nearly as much as you do about the company’s business. So if you don’t share a strategy or context, the task or request is a part of, the team is very likely to be unaware of why this is being asked of them.

How do you think they will acquire the missing information? Amazingly, not by asking you. The answers and, what’s worse, the context, are going to be creatively made up during the lively after-work beer session. The team will work tirelessly to turn the limited information they have into a coherent story while weaving together a lot of assumptions and having no input from anyone who actually knows what’s going on.

Outcome? A request or task will make no logical sense in the context of their constructed reality. As a result, it’s very common for the team to ‘conclude’ that what is being asked is ‘stupid’ and so is their manager. Over time the team’s respect for the manager evaporates, ‘stupid’ requests stop being taken seriously and the whole thing becomes almost impossible to recover from.

3. The team sees the manager struggling and projects it onto the company

It’s much easier than many think to create an impression that a startup is not doing well and cause panic within the team.

I have seen people construct incredible stories around something they saw or heard, which were nowhere near true. Like how did ‘The Doritos order didn’t arrive this week’ even translate into ‘The company is running out of money and I need to look for a new job’?!!! C’mon people, the delivery company messed up, that’s all there is to it!

Be careful with accidentally enabling your team to create a distorted picture based on what someone you put in charge is doing or not doing day-to-day. Employee turnover can be a very expensive overreaction to fake news.

4. Other potential scenarios

There are many more possibilities for a struggling Accidental Manager to negatively affect the team, without even realizing they are doing it.

It’s easy to get overwhelmed by how much work management can be and get swamped by all the things to be learned and all the decisions to be made. However, it’s crucial to remember that a manager’s job is to make the team more productive, not to become a bottleneck.

Time

Figuring things out always has overhead and depending on who is doing it, what they know and how fast they can learn — the time spent can vary dramatically.

In some situations, it might not be a big deal, but in others, it can have a pretty costly impact on the business.

For example, if the company is working with a limited amount of funding (which most are), there is often a short window of opportunity to make a business idea work. If the team takes too long to get its act together, funding can run out.

I have seen this happen and it’s heartbreaking to watch the founder abandon their dream, tell the team the company didn’t make it and find themselves starting over, after spending all that money. Believe me, that is not a situation you want to find yourself in as a business owner.

Alternatively, there might be a narrow time gap to get a product to market. Maybe the industry is shifting and presenting a limited opportunity, or maybe there is a need your team has to fulfill before someone else does. In either case, getting there sooner might be the difference between succeeding and calling it quits.

Many years ago, before online food ordering systems were a thing, my partner built one. He had it completed and working beautifully but ran out of money before he was able to convince the restaurant owners that people would want to order their meals through ‘The Internet’. He is still kicking himself for deciding to manage business development himself. Would he had hired proper help, he might have been a much wealthier person today.

This is why another thing to consider is whether having an Accidental Manager in charge is something the business can afford.

If you are a person in an Accidental Management position, it’s still worth an honest consideration about whether you can get up to speed fast enough. It’s very tough to live with a memory of how your lack of experience tanked somebody’s or your own business and cost 20 people, including yourself, their jobs.

Money

I see a lot of business owners put Accidental Managers in charge ‘to save money’ but end up in the opposite situation.

As we explored earlier, figuring things out has an overhead and unless the company is lucky to have someone volunteer their time, the person is probably collecting a paycheck while doing it. The scariest part is the risk of things not working out in the long run.

I am not suggesting that it’s a bad thing to invest in team members. What is important, though, is to make sure it’s a thoughtful choice, where associated cost, time and risk are considered.

Stress

It can be very stressful, both for a person in an Accidental Manager position and for those who put them in charge, to discover how painful the journey of becoming effective can be. It always takes longer than initially thought and many ‘almost there’ months after that.

On the one hand, the manager is trying their best, but drowning in work and having their head exploding from reading, dealing with the inevitable consequences of mistakes they make, stressing out about being judged by the team and being in trouble with the boss.

On the other hand, we have a founder or CEO who is unhappy about things taking longer and the implications that this going to have on their strategy and planning efforts.

This can take a heavy toll on relationships between executives and the managers they put in charge. In turn, it can destroy a career for people, who were doing awesome before accepting a promotion.

Once again, it needs to be a conscious decision by both sides whether to accept the risk.

Conclusion

There is no right or wrong here. Ideally, people in question should consider these implications beforehand, as opposed to starting to contemplate them when the harm is already done. Though, it’s not always possible.

Whether you are a person putting an Accidental Manager in charge or the one accepting this responsibility, there are huge benefits to proactively acknowledging the boundaries of your knowledge and expertise and trying to find ways to quickly get up to speed.

Getting things working earlier than later can save the team stress, time and money; and the Accidental Manager — their job and face. It can also be the difference between turning your startup into a profitable company and having to abandon ship due to running out of funding.

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Elena Dexter

Elena helps early startups learn how to manage teams in a light, simple and effective way and adopt a ‘just enough process’ mindset and results-only culture.