Bossing it: How to manage management when you’re growing a business

To get their business off the ground and even secure the funding they need, entrepreneurs need to be focused, creative, and just a little bit charming.

But, once there’s money in the bank and they start taking on staff, how do those attributes translate into management? Do good business people make good people people?

Last month, in an article published on Business Insider, James Manktelow and Julian Birkinshaw, co-authors of Mind Tools for Managers: 100 Ways to be a Better Boss, said being a great business leader isn’t about the vision or the work ethic. It’s more about emotional intelligence and tact.

Manktelow and Birkinshaw surveyed more than 15,000 managers and professionals, globally, and found 41.8% named tact as one of the most important skills for managing people in the workplace.

But, when you consider the personality traits of some of the world’s most prominent technology leaders, tact probably isn’t the first thing that springs to mind.

Elon Musk famously advises employees to walk out of meetings that are not worth their while. “It is not rude to leave, it is rude to make someone stay and waste their time,” he says. 

He has also threatened to fire employees who try to communicate through a chain of command. Maybe he’s onto something, but Musk’s approach to his people doesn’t exactly scream ‘emotional intelligence’.

Jeff Bezos sends emails with a single question mark, which acts as shorthand for ‘fix this’. Steve Jobs allegedly called advertising partners at 3am to argue about marketing. These methods may well be productive, but they’re hardly tactful.

So, how can company founders manage the transition from lone entrepreneur to running an actual company, and the people that come with it? We asked three founders what they’ve learnt from their journey of becoming a boss. 

Evan Wong, co-founder of Checkbox. Source: Supplied.

Lead by example

Maintaining the culture and values of a startup is an oft-cited challenge from those that are growing. While founders live and breathe their business, newcomers (understandably) may not.

Evan Wong, co-founder of regtech startup Checkbox, says: “As founders [you] are so incredibly passionate about what you want to build. You really understand it.”

“Not only do new people not have the same kind of information about the company and strategy, intrinsically they’re not able to be as enthusiastic”.

Because of this, Wong says, it’s important to get the company’s values in place as early as possible, but it can also be valuable for founders to get their hands dirty.

“Once you have a sizeable team and you’re leading … at the end of the day you still need to put in some of the grunt work — leading with example, doing the roles you wouldn’t necessarily need to do.”

Wong does “crap” jobs, simply because he doesn’t want his staff to always get stuck with them.

“Whether they’re a senior developer or an intern, sometimes I do the crap work because I feel bad for making them do it,” he says.

Katherine McConnell says that as her energy financing startup Brighte has grown, “it has been humbling for me to be able to execute on my vision”.

She says that she has been surprised at how passionate her team have become about Brighte, saying: “I never expected people to share that same work ethic or that commitment … I don’t know how that happened”.

Manage your time

But one thing McConnell says has taken some getting used to is having to split her time more effectively.

“As the business grows and the priority and stakeholders increase, my time is more valuable,” she says.

“I need to prioritise, plan, have an agenda, and make sure that everybody else is mindful of my time as well.”

While she wants to give every employee the focus they deserve, Brighte’s roster has gone from 18 last year to 50 today, and McConnell has had to learn to prioritise (while also continuing to secure capital to keep Brighte on its growth path). 

Equally, leaders have to consider “the number of direct reports” they have, McConnell says, which “automatically leads into thinking about organisation design and structure”.

“When you’re a startup you’re agile”, she says. But as a company grows, leaders have to consider the best structure to “retain the benefits of speed and communications”.

Brighte founder Katherine McConnell. Source: Supplied.

Don’t micromanage

For founders who are used to spending all day every day working on their business, letting other people take the reins on certain aspects of it can feel a bit like sending your only child off to school.

McConnell says, at the very beginning, there were aspects of Brighte that she particularly enjoyed doing herself, and admits it’s been difficult to see those things taken on by new hires, even though they are “experts focused on that area”.

“You do have to let go. It’s great that we’ve been able to retain and inspire such amazing talent, I have huge confidence in the team and their abilities,” she says. 

Part of this is in understanding the kind of qualities founders want their management team to have.

Workplace safety startup Safety Culture has grown from two people working out of a garage to over 200 today. Founder Luke Anear says he has had to consider a vital question: “How do we support our leaders and support their teams?”

SafetyCulture wants leaders who can maintain high levels of integrity, inspire vision, and hold their teams to account, and Anear says he is serious about “investing in people”.

Wong adds: “A leader really needs to understand that they need to create a very safe environment for their staff … where people are unafraid to contribute and experiment, and where it’s okay to fail.”

This involves empowering people, he says, and understanding what staff members can achieve, even if they don’t see it themselves.

“In practice,” Wong says, “it’s a lot about positive reinforcement and mindset”.

If you trust a person enough to hire them in the first place (and “you should never settle for second-best”), then you should trust them on the job, Wong says. In turn, this creates a culture of accountability.

“Just because your the person who is directing the ship, doesn’t mean your the person making all the decisions,” he says. 

Accept that you don’t know it all

McConnell says a big part of being a good leader is “humility — being genuine about aspirations but also our limitation”.

Brighte’s Series A funding round was led by Atlassian co-founder Mike Cannon-Brookes, and McConnell still meets him regularly to bounce around “practical growth problems and leadership questions”.

The company’s recent Series B funding was led by AirTree Ventures, with co-founder and partner Craig Blair set to join Brighte’s board. It also included Skip Capital, the private investment fund owned by banker Kim Jackson and her husband, Atlassian co-founder Scott Farquhar, and prominent retail entrepreneur Naomi Milgrom.

Surrounding herself with accomplished entrepreneurs was no accident, McConnell says. This latest round wasn’t only about money, it was about bringing in “amazing, wonderful business people [who] hopefully can help fix some problems”.

Anear takes a similar approach, borrowing leadership ideas from Jeff Bezos, Elon Musk and even a tennis coach, and “learning from people who are further along the journey”.

“Everybody’s making it up as they go along. No one has got it figured out,” he says. 

It’s important to show some vulnerability, Anear says, to show that you’re infallible, and to share what you’ve learnt.

“You don’t always have to look like you know the answers,” he adds. 

SafetyCulture’s Luke Anear. Source: Supplied.

Know your strengths (and your weaknesses)

According to Anear, a big part of the challenge for company founders is knowing their own strengths and weaknesses. That includes understanding whether they will make a good leader or not.

“Some make the transition to being a great leader, others hire leaders,” he says.

“Understanding what you’re good at and what you’re not is fundamental both to building a product and building a company.”

Anear admits that he has made mistakes along his own leadership journey, and most of these have come from letting passion and frustration stop him from articulating feedback as well as he would have liked.

It’s important to give constructive feedback “early and often”, he says, so that “little problems don’t become big problems”.

Ultimately, Anear advises any entrepreneur on the cusp of a growth journey to have those tough conversations and talk about the things that might feel “uncertain or scary”. Because in the long run, “everyone responds better”.

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