New Managers Tip 1: Different Perspectives

Elena Dexter
Venture Verse
Published in
5 min readNov 2, 2023

A few years back one of the guys I used to manage called me and said that his wife was thinking about taking on some management responsibilities. Then to my complete surprise, he asked if I could coach her.

At first, I was shocked. I very politely explained that I wasn’t a management coach, my focus was working with teams. But after I thought about it, I figured that if he thinks I am a good manager, why wouldn’t I share what I know? So I agreed.

She had no management experience whatsoever. She simply didn’t know what she didn’t know and couldn’t figure out where to start.

After talking to her for some time, I put together ‘a skeleton’ of what I thought she should research and study more deeply.

I was sorting my coaching folder the other day and came across these materials, so I thought it might be good to share them online.

As I explored in the very first story I wrote here, some people become managers without planning to do so, and in crazy early startup years, that might mean having to just figure things out, quickly!

This series will cover super-simple, but important concepts new managers need to become aware of.

Let’s start with a very common challenge — switching from the first-person view to a business perspective.

Until someone becomes a manager, their main responsibilities revolve around completing their work well and on time.

Priorities might or might not be well-defined and consistent, depending on the company, but they are very likely coming from someone else.

Motivations are mostly personal. I want to do a good job on my project! How well am I paid? Can I leave for vacation and not be pulled into work?

On the other hand, as a business owner or an executive, one faces things like the need to understand ‘the big picture’; identify and mitigate uncertainty and manage risk. Responsibilities include researching the market and competition; thinking about where to find money to finance your product, as well as many more strategic initiatives.

Priorities shift to figuring out how to accomplish more with limited resources.

Motivation is the success of the business and I find that in smaller companies, leadership feels the pressure more sharply. I am not trying to say that executives in large companies are not invested, but it’s just not the same as taking a HELOC against your house and having 8 months to make it work.

I think there is a built-in conflict of interest between the personal and business points of view, as each side considers different (and often the opposite) things a priority.

One of the important roles of middle management, in my opinion, is helping to bridge that gap through:

  • Translating high-level vision into an execution plan
  • Setting priorities, to make sure things are executed in the right order and at the right time
  • Breaking the body of work into pieces
  • Figuring out who does what
  • Making sure each person understands what is required
  • Monitoring progress
  • Course correcting, if needed
  • Summarizing for the leadership how things are going

As a manager, one needs to find the balance between employees’ perspectives/concerns and those of the company.

That requires:

  • Thinking on the right scale, depending on the situation
  • Bridging the gaps in communications
  • Managing up and down

Let’s take a look at a few examples, starting with my favourite ‘manager mindset’ exercise.

Try estimating how much it costs your company to hold a meeting:

  • Figure out what you make per hour (your yearly salary / 12 months / 4 weeks / 40 hours)
  • To make calculations easier, assume that every person in this meeting makes the same amount of money
  • Multiply your hourly salary by the number of people in a meeting

Contemplate: this is how much it costs the company to hold a 1-hour meeting with all of you present. Can the company use this money to achieve something more useful?

Making the right decisions can be emotionally tough, as now you have to consider your relationships with team members against what is best for the business.

Scenario 1:

The security department comes to you and lets you know that your subordinate, who is also your close friend, was caught on camera stealing from the company.

As per the company’s policy, this should result in immediate termination.

Your subordinate doesn’t know they have been caught. The HR department is preparing the documents for their termination.

As a friend, your first urge would be to immediately let them know. Your NDA aside, as a manager you probably shouldn’t.

What would it change if you do? Will it make the experience even more painful for them, as now they have to wait for it to happen and agonize about how it will be done?

Scenario 2:

You are in the middle of a huge project and the team is already behind.

One of your subordinates has an upcoming vacation that has been scheduled a long time ago for a special trip.

Your boss just learned that the team will be losing a pair of hands for 3 weeks in the middle of a crunch. Your boss is having a meltdown and ordering you to cancel your subordinate’s vacation.

Legally, employees are entitled to their vacation and if it was formally approved, the company has no right to just ‘cancel’ it. Emotionally, that’s a horrible move, which might backfire in the future.

But you can also understand how on a small team, where every person is doing 10 jobs, losing someone for so long can simply make things stop. That, in turn, can result in the failure of the project and maybe even the entire business… Can everyone’s jobs be on the line?…

Scenario 3:

One of your subordinates is about to return from maternity leave.

You just learned that the company is having financial problems and will have to do a round of layoffs. She will be affected.

It occurs to you that she will not be able to apply for EI again because she hasn’t worked for long enough to meet the requirements.

You understand that from the company’s perspective, her salary would put a big strain on finances during these hard times.

However, you also know that if she is to be let go, she will be left with no source of income while she is looking for another job and taking care of the baby. What would you do?

In some situations, you just have to do what you have to do. The right choice is obvious, though it can be very tough.

In other situations, there are creative compromises to be found. The key is looking at the situation from both perspectives.

For example, would working part-time be enough to help the new mother maintain her benefits, while she is looking for a new job?

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Elena Dexter
Venture Verse

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.