💌 Welcome to the Newsletter

Happy (albeit belated) New Year to Everyone 🙌

I've been off for a few weeks and it's been wild!

Over the holidays I turned 30 🎂, I got COVID 🦠, and the company I work for raised another $100M making us officially a unicorn 🦄.

With all that fun stuff over I can now focus on the newsletter, and this week we're talking about Leadership Vacuums.

As always, I love reading your feedback and meeting talented and ambitious people so don't hesitate to reply back to this email or book a time on my calendar to chat.

What is a Leadership Vacuum?

Milo is my dog. He's a one and a half year old Samoyed. He's got a lot of energy. And he's a stubborn one. We've gone through multiple phases where he's tried to take over as the leader of the pack and claim Alpha dog.

Recently, we got a dog trainer to fix some behaviors like demand barking and humping. As with most of my lessons in leadership the problem wasn't with him, it was with me:

Dog's need to be led by the Alpha of the pack. If they don't feel confident with the person in charge they will get anxious and, fearing danger, they will take the lead. This can lead to unwanted dominating behaviors.

In other words, Milo was filling the leadership vacuum that I had created.

As you probably guessed, humans are the same. When no one takes the lead, someone has to.

In startups, leadership vacuums can lead to suboptimal outcomes.

Here are three common scenarios where leadership vacuums cause problems:

• The Board

• The Team

• The Customer

Leadership Vacuum #1 - The Board

The relationship with your board is a peculiar one.

On one hand, boards are often populated by VCs who have invested millions of dollars into your business and would like to wield their influence by telling you what you should do.

On the other hand, outside of hiring and firing the CEO, the board's role should be an advisory one. The board should act as additional data input to your decision making, but they should not dictate it.

First time founders can sometimes lack the chutzpah required to lead a board. The presence of experienced operators, only too keen to impart their wisdom, can take advantages of leadership vacuums to control your company.

This is not ideal if you want to lead your startup to success.

"most board members have held powerful roles in the past and may be aching for opportunities to assert themselves. They want to stay relevant, a very understandable human emotion. This is especially true for VC board members, who often have the benefit of extensive exposure to a variety of companies, after serving on many different boards. On top of that, VC investors on your board will consider it “their money” you're spending, which they feel gives them even more justification to cross the line." Slootman, Frank. Amp It Up (p. 176).

It is up to you as a leader to set expectations and create boundaries to ensure your board doesn't cross the line from advisory to authority.

Leadership Vacuum #2 - The Team

When I first started to build an outbound sales team at Spendesk we hired a lot graduates straight out of university. For many of them it was their first professional work experience.

I started to notice a trend.

It was really hard to tell which new hires would ramp up quickly, particularly when adapting to the fast paced environment of a startup.

I realized that we held a lot of unsaid expectations of new Spendeskers. And that was the problem, our expectations were unsaid.

How is someone, who's never worked in a "lean startup" environment where the traditional ways of working don't apply, supposed to know what's expected of them?

To answer this we decided to create a "Life in a Startup" workshop that would be mandatory as part of the onboarding.

The topics covered things like:

• The stage of growth you're joining at: Finding product market fit at series A requires a very different approach to scaling up at Series C

• Ship to learn: We prioritize action over thinking. We ship product fast to fuel our learning over hypothesizing for weeks with no feedback.

• Everyone is a CEO: Everyone exhibits extreme ownership. You are in control of every variable that effects your outcome.

• Ask for forgiveness not permission: You were hired for your ability to solve problems. Don't look for validation to execute.

Along with the expectations we had of new hires, we also had a section labeled "What are your expectations of us as a company?" and "What are your expectations of me as your manager?".

This helped create a clear SLA (service level agreement) upfront.

Everyone knew what was expected of them, and so it was easy to hold everyone accountable. There were no build up of unspoken frustrations because expectations weren't clearly set at the beginning.

In a leadership vacuum, new hires would have had to make a series of assumptions about how to behave and what the work culture was.

By using an SLA upfront there is no need to fill in the blank, just clear concise expectations that reduce anxiety.

Leadership Vacuum #3 - The Customer

Just like an SLA between employees, those of you in sales will be familiar with the concept of an "upfront contract". An example of this would be:

"If by the end of this call you are happy that I've demonstrated we can solve your problem, is there any reason that you wouldn't sign a contract today?"

Upfront contracts are a powerful way to fill the leadership vacuum. They spell out hypothetical scenarios and get consensus on the appropriate action going forward.

If you want to take filling the leadership vacuum to the next level you should set out clear guidelines for how the entire sales process should go.

Many reps fail to clarify, or get agreement on, how the sales process should be executed. If you never create guidelines on what should happen then the customer is left to their own devices.

This is a terrible idea.

• What happens if we decide your product isn't a good fit? Should I ghost you or will we do a debrief?

• What happens if my boss doesn't want to join the demo? Should I lie to you as say that I'm the decision maker, or will we come up with a better plan together?

• How will I validate your platform is a good fit before i buy? Should I test the competition and yours at the same time, or will you help me?

In reality, your customers follow the path of least resistance. And that path is often a suboptimal one that doesn't include key decision makers, and leaves you starved of crucial information needed to close the deal.

You must be assertive in creating your own path of least resistance. One where the customer agrees it will lead to the best outcome.

Don't forget, your customers are not professional software purchasers. They're experts in their own domain, not buying software. They don't know the best way to analyze and buy your product.

So make sure you help them!

Wrapping it up 🌯

Filling the leadership vacuum is not about exhibiting power or dominance. It's about impacting influence through leadership.

You can fill the void by setting expectations.

Expectations may be set in the form of an SLA (service level agreement), or by outlining guidelines upfront and getting agreement on them.

Ultimately, leadership vacuums can only be filled by those who are assertive and confident in the which path to follow. If you are interacting with employees, setting expectations is often enough. After all, they can be fired if these expectations are met.

Working with customers on the other hand, requires you to convince them that your path is the right one.

Only then can you create the path of least resistance.