From faking it to making it in a new role

No-one knows exactly what they’re doing

Here’s a secret about almost anyone taking on an ambitious new role: they don’t know what they’re doing.

But how you go from faking it to making it can have a massive impact on the outcome, and the relationships you make or break along the way.

Let’s compare two approaches:

Richard Branson 

Branson is known for his “Screw it, let’s do it” mentality when it comes to his businesses (and his life).  He’s started dozens of companies in all sorts of industries ranging from music, to airlines, communications, and many others.  Branson says:

“If somebody offers you an amazing opportunity but you are not sure you can do it, say yes - then learn how to do it later!”

Elizabeth Holmes

Holmes had an ambitious vision to change the way diagnostic blood testing was conducted.  She attracted hundreds of millions of dollars in venture capital dollars for her company, Theranos.  By 2014, Theranos was valued at $9B, and Holmes had become one of the youngest self-made billionaires in the world….until everything came crashing down.

She sold investors, customers and employees on her bold vision and tried to “fake it”.  But not only did she not “make it”, she’ll be spending the next decade in federal prison.

So what’s the difference between Branson’s: “say yes and figure it out later” mentality, and Holmes’ bold vision for Theranos?

Holmes had Motivated Blindness: she refused to accept that her vision wasn’t possible and insisted that it was working to investors, and customers when it clearly wasn’t.  She could have instead admitted it wasn’t working (yet), and made incremental progress toward the ultimate goal.  Instead, she lied to investors, and committed fraud to obfuscate her lack of progress.

Branson, by contrast, openly admitted the reality of where he really was (at the beginning of a long journey), acknowledged that he didn’t know exactly what to do, and charted the steps required to make measured progress toward his end goal.

Be more Branson, and less Holmes.

To make forward progress, ask the following 5 questions:

1. When have I done something like this before?

In moments of doubt, it’s helpful to remind yourself of times in your past where you’ve figured it out before.  Experts call this interrogative self talk, and it’s proven to be effective at overcoming self-doubt.  Instead of trying to convince yourself that “you’ve got this”, ask yourself:  

  • When was a time in the past that I was able to surpass someone’s expectations of me?
  • When was a time where I felt overwhelmed, but was able to deliver?
  • When in the past have I been really proud of doing something hard that I wasn’t sure I’d be able to do?

By asking yourself these types of questions, you’re effectively “Googling your memory” for times where you’ve been down a similar path before.  In doing so, you’ll find proven examples of managing situations “like this”, and start building confidence in your ability to figure it out.

2. Where are we, really?

To make meaningful progress, you have to understand where the business really is.  Trust what you heard in the interview process, but verify that what you heard is true.  To do this, conduct internal interviews and external interviews.  First, ask internal employees including the founder(s) questions like:

  • What’s working really well today? 
  • What seems to be broken?  
  • What are you excited about?  
  • What do you believe to be the biggest growth opportunities in the business?  
  • What do you love about working at this company?

Ask customers:

  • Why did you choose to work with us over the myriad of other choices in the market?  
  • What’s working really well today? 
  • What can we improve on?
  • What do you believe to be the biggest growth opportunities in the industry?  
  • What do you love about working with your company?

We’ll get into current state quantitive metrics in future posts.

This line of questioning has a dual purpose:  First, it will uncover challenges, opportunities, and insights that you never would have got from spending time behind a desk.  And second, it re-affirms for customers and employees why they love working with you - strengthening their loyalty to you.

3. Where do we want (or need) to be?

Be clear about the long-term vision, and the immediate goal.  What is it that the team (founders, board, employees, investors) is really expecting of you, and on what timeline?  Get precise around specific numbers and metrics if possible.  If goals or milestones have been pitched to investors or a board, you need to know what those are.  For the moment, ignore how and focus on what.

Good Example: Our vision is to be the operating system for live events.  By December 31st, 2025 we will have achieved $25M in annual recurring revenue, growing at a rate of 30% per year.

Bad Example:  We want to grow as quickly as possible.

This understanding will be foundational to putting together a revenue plan and budget in the future.

4. What do I not know?

Early in my sales leadership career, I thought I had to have all the answers - and that admitting I didn’t know something was admitting that I didn’t know what I was doing.  Later, I realized that having the humility to admit that you don’t have all the answers was freeing.  

However, there is a difference between throwing your hands up and “not knowing”, and clarifying that you don’t know the answer (yet) and will come back with a better answer in the future.  

Admitting you don’t know the answer, outlining the steps required to get one, and then showing progress toward your goal closes the knowledge gap and inspires confidence. 

5. Who can help me?

One of the greatest sources of support that I had in this role was a group of like-minded peers who were in similar roles.  Feeling like I couldn’t confide my real challenges with my partners, I contacted a handful of friends, or second-degree connections who were working on similar growth challenges at early and growth-stage companies.  

We agreed to meet up once a month, over drinks and food, to talk about whatever was top of mind.  Sometimes we entered around issues with hiring, reporting, compensation package design, and even veered into the personal: balancing a big role with life at home.  

One at a time, each person would voice a concern that was top of mind.  Then the group would take 15 minutes and give that person our full focus, share examples of we’d they’ve navigated something similar in the past, and then take one action to help them make progress.

There’s something magical about going out of your way to help others get unstuck.  

Don’t be shy about reaching out to peers, mentors, teachers, or more experienced folks who have been down this path before you.  

Acting as if

Research shows that uncertainty and self-doubt are the rule, not an exception to the rule.  That feeling like you’re "faking it" before you start "making it" is table stakes in big roles that matter.

Asking the five key questions above will help you gain confidence, get clarity on where you are and where you need to be, acknowledge the gaps that need to be filled, and find help to get you there.

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