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Things I wish I knew when I started managing people

To say I didn’t get into management by design is an understatement. At age 21, 3 years into business school after having majored in Chemistry and working at a lab and deciding it just wasn’t for me, I jumped into the adventure of a lifetime: a two-woman business in digital innovation.

The business grew by 8000%+ in 4 years. In a short space of time, we became a multi-million dollar business with investors and a big team. This is a monumental achievement and something I am really proud of. Leading this business has completely shaped me as a professional.

Going from a few thousand of recurring revenue per month to hundreds of thousands comes with all sorts of challenges. You need to scale people, processes and systems on the fly.

Operations is an area I am naturally strong at. As a chemist, I spent a lot of time looking at data to find trends, identify errors and devise better and more efficient ways to get something done. Countless hours meddling with processes and technology, designing experiments, executing, iterating. My previous role was completely focused on analysing data.

In summary, scaling processes and systems was something I was really well prepared to do.

But leading people? Let’s just say that was never my forte growing up.

I sure could inspire others. I organised many protests (getting girls and boys equal time at the good football field during P.E), played a leading role in the student union, organised fundraisers for charities etc. But whenever group assignments were given, I used to offer my groupmates a great rate to complete the full assignment by myself, with a guarantee of a minimum grade of a B+.

I was a nerd with a strong entrepreneurial spirit, a fat piggy bank and delighted classmates, but I wasn’t a leader.

Needless to say that when my team grew from one to five to fifty to nearly one hundred, there was a steep learning curve.

Fast forward 8 years, I was awarded the “Great Manager Award” in Hubspot in 2021.

Not that awards are to be trusted often. I once came across a roadside coffee shop/filling station that claimed to have won the award for the best coffee in Ireland (mm, don’t think so).

But the Great Manager Award meant a lot to me because it’s not a few people in a room deciding who wins is based on who has the most visibility or an award I sponsored that just happened to find me as the winner (surprise!). This is a people’s choice honour. The team members are the ones who vote for the manager they believe does a spectacular job at leading people.

Why am I telling you all of this? Because if I can do it, you can do it too.

Below are some of the lessons I learned in this 8-year journey.

Don’t pretend you know what you don’t know.

As a first time manager, especially if you are managing a team that does a job you have done for a few years, you can feel the pressure to know all the answers. But the reality is, you won’t be the specialist forever.

Whether you work with a product or a technology or a process, things will change in it. As you focus more and more on developing your team and running a business, you will invest more into different competencies and will know less about the nitty-gritty details. And that’s ok.

Of course, it is scary to get a question that you don’t know the answer to. It can be embarrassing, especially if you realise at that moment that this is something you should know the answer to. But avoid the temptation of pretending to know.

Your team knows when you are bullshitting them.

It’s way better to say:

  • That’s a great question! I don’t know the answer to this. Why don’t you talk to “X” person and share your findings with the team?
  • I never thought about it from this angle before. It’s a really interesting question. Let me jot it down so I can ask a few people in the business. I will let you know what I find out in our next 1:1!

When you step away from being the specialist, you create space for other people in your team to take that role. You help elevate senior voices and create leadership in your team.

When you publically acknowledge that someone’s question is interesting and the answer is unknown to you, you recognise their brilliance while demonstrating that you are open and vulnerable about your learning journey. It creates psychological safety for people to do the same.

Don’t hire unexceptional people just because you need someone urgently.

Some of my best decisions as a manager were the people I hired. Some of the worst decisions as a manager were the people I hired.

Hiring the right person takes time and energy.

There have been many times in my management career when I needed someone urgently. Sometimes due to my bad or tight financial planning, others for unexpected circumstances, others for the sheer speed in which my teams were growing. In those times, I felt like I couldn’t go back to the market after not getting a strong contester in an interview batch. I favoured speed versus quality.

I have never not regretted doing this.

It has always ended in getting mediocre results and having to go through a longer and more painful process afterwards.

For that reason, my hiring advice to new managers is to not make offers to “7s”.For this exercise, place all candidates on a spectrum from 1 to 10 that includes competency, culture and potential. This scale is non-scientific.

As a manager together with your HR team (if you have one), you will define the characteristics that are needed to excel in the role you are hiring for. 1 being “definitely not” as the candidate does not possess the competencies, cultural traits and defining characteristics of potential (such as learning agility, coachability, ambition etc) and 10 being a perfect fit.

Why do I say this? Because it’s easy for you to say no to the 1 to 6s, they didn’t demonstrate that they could do the job and you know they are not right. The 8-10’s are clearly great fits and easy to say yes to. You are excited about them.

The 7s are the danger zone. They are the people that could do the job. They are good enough, but not remarkable.

When bringing people to your team, you don’t need the people that can do today’s job as-is. You need people that can do the job one year down the line. People that can drive growth in your company. People that can get the job done when things change and they have to adapt.

You need people that can make the team better, not bigger. Even when you need them to start yesterday.

Set the expectations and don’t move the bar when someone cannot achieve them.

Another mistake I made as a new manager was to lower the bar for people because the job I was asking them to do was hard. Instead, taking on the load to deliver on commitments myself. I even helped the team hit their quota by hitting the phones and connecting with customers about their renewals, upgrades and collections.

Initially, everyone thought it was great to see me doing it. We were hitting the target and it showed that I was in the trenches with my team. But it stopped me from doing other things that were important in the long term.

Career conversations, business reviews, cross-functional engagements, long term projects etc started slipping off the calendar because I couldn’t get to them. After all, I was too busy “smashing target”.

The reality is that I was causing harm to my team in the long run. My top performers didn’t progress as much because we didn’t dedicate time to their development. The connective tissue between departments was breaking and we were working in silos, which in turn meant customers were getting a lot of friction in their experience all because I didn’t spend enough time communicating and working across functions on key priorities.

Meanwhile, those not pulling their weight were staying in the team and the culture started shifting from a high-performance one to a “Daphne will save the day” one.

You get the picture. Not great.

Instead, I learned that my job is to enable that person to succeed. Now, when I work with underperforming people I focus on:

  1. making the expectations very clear (whether they are targets or project deliverables)
  2. helping them understand what is preventing them to succeed
  3. help them craft their own plan on how they will achieve the goal
  4. support them throughout the process with knowledge/resources
  5. hold them accountable throughout the process

I am no longer called a hero. But people that work for me often tell me how I have helped them grow. And that’s better.

Be honest, especially when it’s hard.

Things are not always rosy. Sometimes you hire or inherit >7 people that are not doing a great job. Sometimes people don’t succeed in their own development plans. Other times, great people don’t get promotions because they aren’t ready for specific roles yet.

All you can do is: be honest.

At the beginning of my management career, I had a terrible habit of delaying bad news. I used to say to myself “people are self-aware and they already know where they are at”, or “the work speaks for itself”.

They aren’t and it doesn’t.

As a manager, sometimes you have the unpleasant task of telling someone they are not meeting the expectation, they don’t have the experience, they are not prepared, or you are not seeing them putting the work in.

I am a big fan of feedback and I like it given to me straight with no colouring. I take very little personally. Not everyone is like me. Knowing your team at an individual level will help you decide how you will frame this hard conversation. The key is that they know you are coming from a place of wanting to genuinely help them.

After hard conversations, some people left my team and found more fitting roles, others were able to succeed by investing time and energy in the right places.

I have never regretted a difficult conversation. But boy, have I regretted delaying one!

Don’t promote people that don’t add to your culture

Culture is the glue holding your business together. It’s why people come, it’s why people leave. It attracts customers and partners, it also sends them away. So developing and protecting your culture is vital for the long term success of your business.

I have hired incredibly smart and talented individuals that were the right person for the role, but the wrong person for the company. They didn’t live the values. They didn’t act in the way that was expected from employees of the business. Some of them I hired fully knowing I was entering into cultural debt but bringing expertise (refer back to lesson 2).

As if it wasn’t bad enough to hire the wrong person, I have also promoted the wrong person. At the time, I needed boots on the ground on a territory where this person was operating. They had incredible results. I needed to act quickly because we had a major hiccup with a partner. I weighted my known pros and cons and decided to offer the person the management role. Their responsibility was to lead the region and build a team under them to service one of our largest partners.

At the time, I was leading a team for only one year and I didn’t understand the importance of culture when scaling a business. Over time this person created an office that felt completely different from the rest of the organisation. With cultural values that were in conflict with the business and many problems emerged from the experience offered to customers and partners through our services.

After many difficult conversations, countless overseas trips and terrible nights of sleep, I turned the situation around. It taught me a valuable lesson: cultural debt is paid back with compounding interest.

It’s seldom worth it.

So when promoting people to leadership positions, never ever compromise on culture.

There are hundreds more lessons I learned in my people leadership career so far. Many I’d love to share in the future around mentoring, recognition, pushing people out of their comfort zone etc. I am sure I will learn many more in the years to come.

By summarising these impactful lessons, I am hoping to help new managers with the obstacles they might be facing and perhaps shine a light on the behaviour they need to change to become great managers.

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