What professional sports can teach you about hiring and setting up new leaders for success

“I wasn’t a Phil Jackson fan, you know, when he first came in,because he was coming in to take the ball out of my hands. Doug put the ball in my hands,” says Michael Jordan, the greatest NBA (National Basketball Association) player of all times, in the popular documentary series about Jordan and the Chicago Bulls’ 1990s run, titled “The Last Dance”. The series co-produced by ESPN and Netflix, centres on Jordan, one of the central figures responsible for making NBA famous across the world in the 1980s and the 1990s.

(It is worth noting that Jordan’s team was one of the co-producers and he himself retained the rights for final cut and editorial control.)

The idea of bringing in new leaders

In a surprise move, Chicago Bulls, an American basketball team, replaced its head coach Doug Collins by assistant coach Phil Jackson in the 1989-90 off-season. And, Michael Jordan, did not like the change.

In a surprise move by Chicago Bulls, replaced its head coach Doug Collins by the then assistant coach Phil Jackson. And, Michael Jordan, did not like the change.

Scottie Pippen, who played an important role in transforming the Chicago Bulls into a championship team and popularizing the NBA, best describes the reason, “Phil took over and just had a different approach. Doug’s approach was more catered to Michael, and Phil’s approach was more catered to the team.” 

This anecdote describes a classic situation in the startup world. The founder does not want to let go of the reins despite hiring new leaders to manage some key functions in the scale-up phase. It sounds easy enough but ask any founder, it’s tough. In this case, Michael Jordan was used to being the dominant scorer – the one who puts the ball in the hoop – in the first few years of his career. Now, he was being asked to give that up.

 

 

The founder (with the help of the core team, of course) has built a business from the ground up, has spent working 16-20 hours a day, converted a mere idea to a product or service, achieved product-market fit, got the initial set of customers and the company has taken off! To give up some of the functions that the founder was doing and allowing the new leaders to take over could feel like giving a part of your identity and even a part of yourself up.

As part of Freshteam’s Leadership Series, we got Jill Sinclair, an executive coach and author, to talk to us about when startup founders should bring in leaders and how they can set them up to drive business growth to ensure that their organizations are on track to go through the various stages of scale-up.

 

In this session titled “Leaders – How to Get Out of Your Own Way”, Sinclair talks about the following points:

  1. When and how founders of companies that are in the scale-up phase should bring in new leaders into their organizations, specifically functional leaders
  2. What screening and hiring criteria should they employ when they expand their leadership teams
  3. How should founders prepare themselves mentally to let go of some of the functions they had been taking care of from the beginning and allow the new leaders to take charge
  4. How should the role of the founders scale up as the company scales up and new leaders come in
  5. How does this change the organizational design of the company
  6. How founders and new leaders should align their expectations

 

1. Re-evaluate your goals before hiring new leaders

Lesson #1 from Sports:

“Think of it like a new hockey team starting out and it’s draft time and you want the best that your money can buy at this time. You want to find a captain who is a leader that will help you build the team, help to create a winning culture and someone that others will respect and listen to,” says Sinclair, who is quite a natural in drawing parallels between the worlds of sports and business. 

“The owners of the hockey team don’t play on the ice, they let the players do what they need to do.”

The very first step in the entire process of hiring new leaders to help your business grow is to look at your goals and those of your company. Sounds simple enough but an often-missed point, this is extremely critical as this enables you to work backwards from your goals and also helps you to answer the rest of your questions: what, who, where, how and when.

While mulling over how far you’ve come and where you want to reach or take the company to and you realize you need somebody who is more efficient and has better skills than you do to take your startup to the next level, that’s perhaps a good time to bring in those new leaders. Obviously, you have to be honest with yourself.

Sinclair says there’s no magical timeframe to hire new leaders but when you’re thinking of doing so, she suggests you have at least six months’ reserves in your bank account that will help you cover costs. The person you hire is hopefully the right person and is able to increase your company’s revenues.

2. New leader must be innovative and also scare you a bit

The first criterion when you hire a new leader must be culture fit and second, innovativeness. Is this the kind of person with whom you can spend time with? However, Sinclair says that doesn’t mean you need to be friends. 

You would obviously look at the proficiency levels of the new leader you hire. What happens if somebody is proficient and has all the required skills but is unlikely to be a culture fit? She says that it won’t work because it would start to be a hindrance as you go along. Not that you are always going to get along with the people you work with but if the personality styles don’t match, it would start grating on you and as a result, the new leader would end up not doing well.

The first criterion when you hire a new leader must be culture fit and second, innovativeness.

One of the things that Sinclair has done to pick the right candidate as a new leader for her clients is ask them this question: So imagine this. We’ve hired you. And right away, we’re going to have a dodgeball game. Just tell me what your team would look like and I just leave it there.”

She says that usually this isn’t a question that people expect and gives her a chance to assess how quickly their minds are able to adapt.

 

“And the appropriate answer is if somebody says, you know what, I’m going to build a team with someone who’s really good at throwing with their arms; another person that’s going to be really good at ducking and getting out of the way and you know what I want to win. And I want to have, you know, good conversations with our team to make sure we have some strategies. They’ve just formed a winning team and they also understand how to pick people with different traits and different skill sets, right. So, there, you have someone that knows how to win, but also knows how to build a team,” she says.

The leader you hire should scare you a little bit!

She also believes the leader you hire should scare you a little bit. Why? Because if you hire someone you’re too comfortable with, it’s easy for you to continue acting like the leader and continue calling the shots, which isn’t okay.

3. Hire your new leader, trust them and let go

That sounds easy and you may wonder what’s so complicated about that? Oftentimes, startup founders have blinders on and they might overlook some very basic or simple aspects, such as letting go.

Consider this story of a company Sinclair has worked with. One of her clients, a two-partner firm that has been in business for 15 years and had around 20 employees, had a self-employed consultant come in to manage their books. As Sinclair started working with them, she got to know that the accountant didn’t have any authority. She couldn’t sign checks for even $5,000.

Each time a check needed to be signed, it was couriered to the partners who signed them and then dispatched to whoever those were intended for. “So literally, they were spending all of these hours that they could never get back because they didn’t give her the authority. First of all, if you have someone that you’ve hired to help you with your accounting, you need to trust them. And if you don’t trust them you’ve hired the wrong person. So you had someone for 15 years. You need to give them some sense of autonomy,” she says.

Lesson #2 from Sports:

Imagine you’re playing baseball and you’ve got someone new in the team. They go up to bat and they tell you they’re not comfortable batting and that would you do it for them? You say cool and do it. Then that person says that they do not want to run to the first base and you literally pick this person up and bring them to the first base and then, the second base.

You are playing the entire game for them. If the situation is such that you’re forced to play their game for them, then, you’ve hired the wrong person.

4. Know your strengths/weaknesses and hold yourself accountable

So as your organization is scaling up and you’re considering hiring or hiring new leaders to take your business forward, the founder needs to scale up too. Though much is spoken about scaling of the organization (which is important), the scaling up of the founder is the other side of the coin that is sometimes ignored.

To determine this, first, you need to have a clear idea of what your goals are, where you want to take your company to and if selling it at a later point of time is there on your agenda. This would help you understand how you need to scale yourself and in which direction you need to grow.

One of Sinclair’s clients (the company had two co-founders) requested her to help scale their business. After some deep-dive sessions with both the co-founders, Sinclair realized that one wanted to scale the business only to sell it and start another one while the other co-founder wanted to scale it as it was part of his identity. In case there is more than one founder, you need to be in alignment with each other about why you want to scale your business.

When you’re looking to hire new leaders, you need to have a clear answer to what your business goals are, what your personal goals are, what are your strengths and weaknesses and what skill sets would the new leaders bring in. You need to clearly map these out with each other in order to scale yourself up.

When you’re looking to hire new leaders, you need to have a clear answer to what your business goals are, what your personal goals are, what are your strengths and weaknesses and what skill sets would the new leaders bring in. You need to clearly map these out with each other in order to scale yourself up.

As a startup founder, you would probably be talking to customers, closing sales, coding, hiring and picking up pizza for your team, but once you’ve pressed the accelerator, you’re in the scale-up phase and you cannot stick to your old role. From being the Jack of all trades, now you’re the captain of the ship taking it in a particular direction.

Another client of Sinclair signed her up to help them scale up their business. She visited their office once a week as a consultant to take them through this phase. “And I come into the office one day and I guess he had forgotten I was coming in at this certain time. And guess what, one of the owners was doing inventory!” says Sinclair.

“The owner of this large company was doing inventory because guess what he was doing? He was putting off a very important decision that he had to make. And he apparently been doing inventory all morning with the executive assistant,” she says. This emphasizes the significance of holding yourself accountable and cruising ahead instead of stalling on important decisions and Sinclair says having a CEO or somebody at the helm would have made accountability easier for the owners of businesses, especially in such situations.

5. Tell your team you’re not the one calling the shots anymore

When you’ve hired new leaders to steer the ship on a particular course, ensure that the roles and responsibilities of the new leader(s) as well as yours are clearly established and communicated to the rest of the team. Tell them who would be responsible for what and who would be reporting to whom.

“You have to understand and establish from the very beginning that if someone goes behind the new CEOs back, that’s not acceptable just because they’re comfortable. And maybe, it’s almost like the mom-dad situation, you know? Maybe, dad is the easygoing one and you know, you go behind mom’s back and say – can I have this?” she says.

You have to understand and establish from the very beginning that if someone goes behind the new CEOs back, that’s not acceptable just because they’re comfortable. And maybe, it’s almost like the mom-dad situation, you know? Maybe, dad is the easygoing one and you know you go behind mom’s back and say – can I have this?

In her experience, Sinclair says she has seen this happening time and again and the owner of the business ends up feeling validated or worse, loved. “It’s not about being loved, it’s about business,” she says.

Lesson #3 from Sports:

Mahendra Singh Dhoni, one of the most successful captains of the Indian cricket team resigned as the limited-overs game captain ahead of the One-Day Internationals and Twenty20 Internationals against England in January 2017. He later explained the reason for giving up his captaincy had been well-thought out and not a hasty decision. For the uninitiated, he had said that the reason he had resigned was in order to give the new captain (Virat Kohli) to prepare a team well ahead of the ICC Cricket World Cup 2019.

Dhoni, regarded as one of the best captains in modern limited-overs International Cricket, was still available for selection as a wicketkeeper-batsman for the next big series in 2018. This highlights the importance of letting go of the reins and at the right time and startup founders may draw parallels in making similar decisions, especially while transitioning from the startup to scale-up phase.

Lesson #4 from Sports:

Sinclair again goes back to baseball to explain the importance and the need for each person to stick to their roles. “Like a baseball team, each player has a very specific role – pitcher, first base, second base, etc. They all know without a doubt what their roles are. You don’t have the outfielder coming in to take on the back catcher’s role. That makes no sense,” she says.

6. Have blunt, honest conversations and align expectations

Sure, you need to be nice to those you work with but that shouldn’t stop you from having honest, open conversations with them. Do ensure your exact intentions are laid out. Clearly mark the areas where you as the company founder would have a say and those in which the new leader has the authority to make decisions. Not only are expectations set in this manner but it also expedites the workflow processes and there are no unnecessary delays or blocks.

In the beginning, you might want to loop them in given that it’s your business and they are new to it and they would want your support to get onboarded. But beyond that, Sinclair says they are supposed to figure it out because that’s why you hired them in the first place. If they can’t, they may not be a great hire.

Not only should the demarcation of roles be written down clearly with no room for any ambiguity but this should also be clearly communicated to the employees of the company. The new leaders’ job descriptions must be well-defined along with timelines, which are held at a high level of accountability.

“Touch the paper only once,” says Sinclair. If you are spending time double-checking the work done by the leaders you’ve hired, remember that it would cost you a lot financially. “If they are not fulfilling their responsibilities, let them go. Hire slow, make sure you’re hiring the right person and fire fast.”

Touch the paper only once. If you are spending time double-checking the work done by the leaders you’ve hired, remember that it would cost you a lot financially. If they are not fulfilling their responsibilities, let them go. Hire slow, make sure you’re hiring the right person and fire fast.

When you bring in new leaders, understand what their expectations are and what their plans are and then marry their ideas with yours. Make sure there are no assumptions in any of your dialogues.

Lesson #5 from Sports:

Take the example of Lewis Hamilton, a six-time Formula One (F1) World Champion, and Toto Wolff, Team Principal and CEO of the Mercedes AMG Petronas Motorsport Formula One Team. They joined hands in 2013. Since 2014, Mercedes has won six consecutive championships – a record by any F1 team and Hamilton has added five titles in this period to become the second most successful driver of all time.

“We have disagreements, but we’ve never had a bust-up or anything like that. We’ve just always been very transparent with each other, whether you like or not. I think that’s why [the relationship] is as healthy as it is,” Wolff has reportedly said, on the relationship he has with Hamilton.

The same report quotes Hamilton: “Communication really is so important. We find that nowadays that as soon as there’s a problem we pick up the phone and we sort it out straight away.”

Perhaps, such basic yet powerful strategies have worked well for their relationship and their spectacular performance on the tracks.

Lesson #6 from Sports:

Sinclair says, “How many times have we seen two outfielders in baseball going in for that pop fly only to have both of them crash into each other or let the ball drop in between? Why did that happen? No communication. No setting of expectations. Just say, “Tony, it’s your ball man. Catch it” and then step aside.

Jordan and his evolution as Chicago Bulls’ leader

Lesson #7 from Sports:

With Jackson’s entry as coach, Chicago Bulls got introduced to triangle offense (an offensive strategy in basketball which Jackson used to win 11 NBA finals with the help of his assistant coach, Tex Winter). 

In a nutshell, this proved to be a turnaround point for the Bulls. According to the ESPN-Netflix documentary, it took a while for all the players to get adjusted to the new style of playing. The players evolved and began playing to their strengths. “Instead of being in Michael’s shadow, Scottie was starting to blossom as one of the top players in the NBA,” says Will Perdue, one of the Bulls’ players, in the series.

Jordan went from:

Scene A: 

Jordan: ““There were so many times Tex used to yell at me, saying, “Move the ball. Move the ball.” He (Tex Winter) says, “No “I” in team.” I said, “There’s an ‘I’ in win.””

to

Scene B:

BJ Armstrong, who won three NBA championships as a point guard for the Chicago Bulls, says: ““He made a conscious effort to say, “No individual is gonna be the team.””

Jackson sums it up well. ““That’s a special thing to have happen, when the largest icon that the NBA’s ever had understands that, “I don’t have to have the ball in my hands all the time.