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Boss vs Leader

Two approaches to managing company culture & team

Many of us in management roles, we’ve never had training on how to do this job. We’re literally making it up as we go or depending on others to help us in how to go about being in these roles.

Read Time: 8-9 minutes

By: Heather Wentler – StartingBlock Madison Entrepreneur in Residence 

“I’m a Boss”, “Boss Lady”, “World’s Best Boss”, “That’s Boss

We’ve all seen these statements thrown on every kind of merchandise or been called them by those we work (or live) with. The dream for many is to be the boss or your own boss when it comes to our career moves and decisions. But is being the boss really what you want to be?

If you’ve been in management or C-suite roles you probably know there’s a love-hate relationship that comes along with it. There’s a real sense of power when you are within these roles. But your power can also be your kryptonite.

The pay that usually comes with higher-level positions often draws people to want to be a boss or leader. I also believe that people view high-level roles to have more flexibility or less workload because they have others to support their work. This is where being a boss vs a leader comes through.

I’ve met and worked with many people who have left their management or executive positions to work as hourly workers or started ventures that fit their quality of life who have said at the end of the day, the pay wasn’t worth what it did to me as a person.

Being higher up on the company list means you’re making decisions constantly throughout the day. We spend every moment from when we’re in work mode (and sometimes before and after that) preparing or making rapid-fire decisions based on problems that are in front of our faces. We also have to evaluate which problem is worth putting our attention to at that moment and which we can rubber stamp, or just approve without lots of mental thought because we don’t have the bandwidth to put more energy into it.

It all adds up.

For many of us in management roles, we’ve never had training on how to do this job. We’re making it up as we go and depending on others to help us figure out how to go about being in these roles.

Listening to what’s not being said

I’m going to preface this by saying going forward in this article when I use the term “staff” I mean those who are employees or interns of the company, and “team” means staff, contractors, and business support agencies (ie: accounting, legal, web developers).

A lot of the work I’ve done outside the day-to-day of running an organization over the past two years has been around how to make Doyenne sustainable and also how to build a culture that’s not running on fumes and sucking the energy out of the team. Transferring my daily marathon of decisions needing to be made into measurable and impactful outcomes has created boundaries and doesn’t make additional workload for others. It’s made saying “no” or “this is how much I can give”, and questioning others’ expectations of me a lot easier without the guilt too.

I started listening for key phrases coming from myself or staff members to recognize decision fatigue and how I was overall managing and supporting the team

  1. I don’t have capacity

  2. Who is going to add this to their list of things to do?

  3. Is this something we’re going to be evaluated on for job performance?

  4. I don’t make enough for you to ask me to do all this

Boss vs. Leader Test

There are distinct differences between being a boss versus being a leader. Take a moment to test this theory.

  1. When you hear the word “boss” what image or words come to your mind?

  2. When you hear the word “leader” what images or words come to mind?

Compare the two lists. Which do you see yourself as? Is that where you want to be or would you like to be in the other category?

When you think of the word “boss” do any of the following words come to mind or show up on your list:

  1. Task Manager

  2. Time Manager

  3. Sets performance expectations

  4. Provides feedback

  5. Decision Maker

  6. Provide direction without asking for input from others on the team doing the work

Someone who is looking over my shoulder, making sure I’m checking the boxes of my job and making them look good for whoever they’re held accountable by. They usually also create more work for others in order to make themselves look impressive or needed by others. Notice that a lot of the characteristics I described are the same as someone we could also be defined as a bully. My mental image is of an overall unhappy person, sitting behind a desk and trying to intimidate me when I speak with them.

A friend of mine works remotely for a national company. They had worked virtually pre-pandemic because the headquarters office is in a different state, but when everyone went virtual the company put a mouse cursor tracker software onto the company network. Meaning that employees’ mouse and cursor movements were being tracked whenever they were logged on as working. If it sits still for too long, they get a message from someone asking if they were in a meeting, taking a break, or not working. When this is a measurement tool for job performance, do you think the employee is feeling like their input matters beyond $$ into the company?

When you think of the word “leader” do any of the following words come to mind or show up on your list:

  1. Focused on the overall development of team members and full team

  2. Encourage strategic thinking, innovation, and action

  3. Considers others’ feelings and checks in with the team as to their experience

  4. Performance reviews are comprehensive and beyond tasks achieved or metrics hit

A leader is someone who includes others in the decision-making process and listens openly to ideas. They give constructive feedback as to how to make good decisions and connect the ideas into strategies already in place or new strategies to support the development of long-term success. This person looks much more approachable in my mind’s eye. They invite me into their office or make time when I say I need help, ask about how I’m doing with the expectation of more than an “I’m fine” response, and encourage me with what I’m working on.

A few years ago I had taken a short-term consulting gig at a local company. I was having a rough time finding my place and voice within the team I was working with because my talents and professional background were very different from others. I remember one of the founders asking me into a conference room one day to ask how I was doing because they noticed I was withdrawing and not speaking up as much as I had in the past. I felt noticed, and listened to at that moment and realized that I was part of the team. My voice mattered and they were going to be a champion in helping me feel included.

Blended Model Leads to Overall Success

It’s a lot of work to make changes to be the best manager/director you can be. As I continue to say, change has to start at the top. Everyone has to be willing to make personal changes as to how they interact and set expectations for others. Everything from written communication to vocal tone and facial expressions when engaging with others to processes for job performance and day-to-day expectations have to be modified.

Setting expectations and holding people accountable in a “boss-like” style can still happen, but the approach may look and feel different than what has been used in the past.

Other tools you can implement to be a supportive leader:

  1. Create tools for job roles and job performance evaluations that look holistically at the position and give space for the employee to give their input

  2. Check-in and check-out meetings that ask how they’re doing as people and not just as workers

  3. Have an open-door policy. Space where they can vent their frustrations in a constructive way and also create dialogue for going forward. Also, create space for “I don’t want to talk about this right now” and “This conversation is over” to show mutual respect and empathy

  4. Team non-work gatherings. If you can afford to get people out of the office and do something fun you’ll be amazed at how much work actually goes on during these opportunities. These can be done virtually too if your team is not all local or you can’t afford travel expenses to bring everyone together

  5. Give recognition to what others contribute.

  6. You can’t accomplish what you’re doing without all involved. Your team is invested in the venture just as much as your investors and shareholders

  7. Never stop learning. Continue to seek new knowledge, approaches, and guidance as to how you can evolve and be the best leader you’re capable of.

  8. Create clear and defined company values and principles that are seen and felt across the way the company operates and presents itself to the public

As you implement change, you’re likely going to see people push back or leave. Sometimes this is for the best because they’re not a good culture fit. Other times you, as the leader, need to step back and ask yourself, am I making the right decisions? And always, you’re going to feel isolated because you have to make these decisions and deal with the reactions from others when decisions are made.

Being a boss or leader is not easy. It’s also not for everyone. Having key people who you trust, believe in you, and support your leadership style is priceless. Even more so if they’re part of the decision-making process within your company so you feel united and not so alone. Some people will manage very differently than you, even with the same operational guidelines in place. That’s okay, as long as it fits with your company culture.

When you sit down at the end of the day are you proud of the decisions or way you lead for the day?

  1. If not, why? What changes can you start to make?

  2. If yes, that’s awesome! How are you going to continue that going forward and not fall into the decision fatigue marathon again?

What to talk more about how to lead and develop your company culture? Or to talk about anything else related to running and working for a startup venture? Schedule an Office Hour with me.


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