Meet the New Boss, Same as the Old Boss?

Steve LudwigLife StuffLeave a Comment

wooden tiles spelling out "in lifting others, we rise".

Most people are not prepared to be the boss of an organization.

It’s not a character flaw; rather, as much as we talk about leadership in business circles, you can’t know what it’s like to be in charge until you are.

It’s a big responsibility that people’s mortgages, their kids’ college educations, and vacations to Disneyland have a lot to do with how well you run your company.

As a B2B tech startup founder, you are providing leadership every day and, if you are like most of us, you aren’t really sure if you are doing it right.

One of The Right Five co-founders, Neil, had two large management roles before becoming the CEO of a tech startup. Each role provided important leadership lessons. Here are a few:

  • The notion of “boss,” the command-and-control style, is mostly dead. To compete for the best talent, today’s highly skilled workers are looking for leaders, not bosses. 
  • Contemporary leaders are ones that empower their employees to make decisions, provide necessary tools and training, and set a clear vision—a North Star of where the work is leading. 
  • When you make hard decisions that might be unpopular, you have to provide your team with solid reasoning behind those decisions. This builds trust and loyalty. 
  • Everyone has barriers to achieving their potential, whether real or perceived. When working with individuals, start with “tell me why you’re not as successful as you would like to be”. You’ll be amazed at how trivial some of those “barriers to success” are. Remove them and then, while giving them support where needed, see if they sink or swim.
  • You must deal with low performers, fairly of course, because if you don’t it’s demoralizing for the team. The low performer might not be in the right role, they might not have the right skill set, or they have a bad attitude. Whatever it is, it needs to be dealt with so people that are doing the heavy lifting don’t have to put up with sub-par performers. 

Some key takeaways from Neil’s time as CEO:

  1. Board meetings suck. They suck less if you’ve spoken to all board members ahead of time so the meeting itself is more of a formality than a discussion. And, if one board member is especially difficult, don’t let them occupy too much of your time or energy.
  2. Early investors don’t necessarily have the same motivations/good intentions you do. For example, suppose your seed investor is raising money for another fund just as you’re trying to raise a round. In that case, they’re going to encourage you to maximize the valuation of your company in your current round (“look how great our portfolio companies are doing”). That strategy can often backfire on you when it comes to later rounds when you have an unrealistic valuation to defend/exceed.
  3. Even CEOs have personal problems. Try to minimize the number of variables in your life. You might not want to have a child, move, and risk all of your life savings at the same time. If you do, you won’t be secure enough to deal with all the ups and downs a startup has. That means you might bail early and kick yourself for a long time afterward.
  4. Remove barriers to your own success. This requires self-knowledge. There can be a lot of stress in a startup, so you have to know where your own land mines are, deal with them, and also know how to invest in areas that give you energy and make you flourish. If you are not clear on what those things are, there are a number of really good personality tests on the market that help you gain better insight into what makes you tick. 
  5. It can be lonely. Get someone or something—a coach, a therapist, a mentor, and/or join a group of other teach leaders—that can provide you the support you need. You are likely not the only one dealing with an issue, others are likely struggling with the same thing. Having people that understand (a great spouse should only be expected to do so much) and can provide encouragement and support can make the difference between success and failure.  

And, of course, don’t forget to hire a Pathfinder as your first salesperson. They have the best chance of success in helping your business grow and meet its potential. 

Want to find out how The Right Five can help you find and hire your Pathfinder? Watch this five-minute overview and demo of The Right Five or send us a note and we will set up a meeting.

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