7 Ways to Diligence the CEO

“Every CEO is crazy… You just need to understand if it is the type of crazy that you work well with.”  Top CRO

When you pick a company, whether you are working for the CEO or not, they drive a ton of the culture at the company.  

“Enough with trying to be central casting.  I’m going to be exactly who I am.  And we are going to make everyone else work around who I am.  It is a lot easier being who you are.”   Brian Halligan, former CEO of Hubspot on Shane Parrish’s podcast

There has been a lot written about founder mode.  The benefits of founder-mode are the innovation and urgency that founders can drive.  However, you should also be thoughtful about the risks and upside the CEO will have on the company, and hence on your career.   Many executives we talk to who have short stints cite the negative culture of CEOs. 

Below are key considerations to think about when joining a company and how to do diligence on the CEO.

If you earlier in your career we recommend you focus on the company trajectory and who you work for but if you are VP+ definitely read this article before you join a company.

#1 What type of CEO are they?

People often talk about a “sales culture” or “engineering culture”.  This all flows from the CEO and what they care about and how they are wired.   Depending on the role you are looking at, here are some questions to ask:

• Are they a ‘product CEO’ ‘GTM CEO’...?  Where is their background (i.e., product, sales), as that will probably define how they tick 

“CEOs that aren't wired to the function you are joining usually come in two flavors:  1. (Rare) they are aware of their blind spots, will give you the space to operate, and will hold you accountable for results 2. (Common) they aren't aware of their blind spots, will try to over-correct/micro-manage you, which will slow you down, add bloat to your work, and will end up working against you despite their best wishes.”  Top C-Level Exec

• What do they value?  Do they appreciate strategic analysis and analytics, product innovation, breaking things…

• Are they learning on the job?  Are they a first time founder or experienced CEO

“One of the biggest decision points to make in your search is will you work for a founder CEO.  Many more seasoned executes will not.”  Whispered Alumn

#2 Does the CEO value alignment?

You should not be looking for a consensus drive CEO.   “Consensus is the enemy of great” 

But you should understand how aligned the CEO is with their executive team.  Great CEOs can bring urgency and drive rapid change.  But they can do this in one of two ways

1. Force of CEO personality

2. Building an aligned executive team that can move quickly

The first is definitely a red flag as the company scales, as it means the company will bounce back and forth on strategy, and the company will be at the whims of ideas from the CEO.  You will often see lots of politics at the C-level.  Here are some questions to assess this:

• How is the company strategy set?  Is it an aligned executive team or set by the CEO

• Does the CEO empower their executive team?  Can the VP/exec layers make decisions, or do they have to wait for / get overridden by the CEO

• How does the CEO make decisions?  Do they care/appreciate process and structured decision making.   And… how do they communicate these decisions

• Is the CEO aligned with the board on the company strategy?  This is often something people overlook, but can predict challenges in the future if alignment is lacking

#3 How does the CEO think about feedback?  

Every CEO says they want feedback.  Not all have the emotional maturity to accept and learn from it.  You should quickly assess how they give and get feedback.  

• Can you disagree with the CEO?   Tell me about a time you did

• How does the CEO take feedback?  What is some feedback you as CEO have received from your executive team and what did you do with it?   (To the exec team). What is some feedback you've given the CEO? How did (s)he respond?

• How do they learn?  What's a time when a bet or a decision you made didn't pay off? Why not and what did you do about it?

• Do they create a culture of feedback?  Do they look to hear input from the company through tools like Culture Amp / Lattice or do they refuse to use these

#4 Is the CEO right for this stage?

Many founder CEOs stay in the weeds long after they should and don’t grow as a leader.  This can cause ripple effective including politics and poor execution.   See this terrific podcast from Brian Halligan on the stages of a company (start at the 14:50 mark) and don’t forget to check out our article on company stage.

#5 How do they think about GTM?

If you are a GTM executive (this is where Whispered focuses) you need to understand if the CEO will be involved in GTM and how you can leverage them.  

• Who is the GTM Decider?   Who owns go-to-market decisions?  If there are disagreements between sales/marketing for example who makes those decisions (the CEO, CRO….)

• How does the CEO view enablement?  Do they just tell teams how to sell better or do they truly leverage enablement

• How does the CEO view the company's brand?  Do they understand the importance of brand and how it works with demand gen? How do they view AR and PR?  If you are looking at Marketing roles, do they value PR and will they invest their own personal time to forge relationships with journalists, to prepare for media briefings, and to deliver those briefings?  Do they have the presence and charisma to deliver them well?

• How does the CEO want to be involved in sales?  Do they insist on doing demos (run away fast!)  Are they there to help with big deals and retaining key customers? Do they value sales or do they think that if  Eng builds a great product it will just sell itself? You may laugh, but many founder product oriented CEOs think that. Does the CEO have the gravitas and customer centricity to get on a call with a prospect and help close the deal?

• Do they understand GTM metrics?  Do CEOs understand forecasting, pipeline coverage, marketing funnels.  If they don’t but still want a say in key GTM decisions avoid these situations

#6 How transparent is the CEO?

No CEO can be totally transparent especially when they are facing challenges themselves with the board but those who default to transparency (with at least their senior team) are the types of CEOs that inspire confidence in good and bad times. 

• Do they share exec level data?   Do they share board decks / GTM data or do they hoard it

• Will they let you see data before you join? A confident / transparent CEO should be fine with you diving deep on metrics before they join.  We’ve seen executive GTM leaders ask for and get early access to web metrics, pipeline… 

“If you are joining at the CXO level, any CEO worth their salt should give you all the data you need to make a decision. Revenue, growth, burn, profitability, COGS, etc. Yes, they can't give you salary-level data unless you are the HR/People leader, but they should ensure you have a full view of the business.   Anyone who refuses to do so, especially after they've given you an offer is either inexperienced (bad) or is hiding something (worse).”  C-Level Exec

#7 How do they treat others?

There is that classic story about going on a date and watching how someone treats the waiter.  Evaluate your potential CEO similarly.

• What do they say about people when they aren’t in the room?  Are they telling you negative things about the rest of the executive team before they even know you

• Do they talk differently about junior people?  Is there an “in-club”

Other Flags to watch for

Below are some specific flags that should guide you to dig deeper

• High executive turnover

• Glassdoor/Indeed reviews

• Insights in Whispered’s company database

• First-time CEO/Founder:  These often have been successful out of the gate and haven’t had to learn how to build culture and alignment.  Dig in on these.

If you have concerns about the CEO but still think the company is worth going to, think seriously about whether you want to work directly for the CEO or take a #2 role where you have a buffer for air cover.

Separately, don’t forget to think about where the company is in the journey and who its investors are.  Here is a terrific read from GTM fund on picking winners.

Ways to research the CEO

VCs, unfortunately, don’t think critically about the quality of the CEO.  They are focused on growth and have often been some of the worst enablers of bad behavior.  So if a VC says “the CEO is awesome,” don’t stop there… Dig deeper. VC also sees a monetary perspective vs a cultural one.  

In addition to asking the CEO and exec team the questions above, you can also:

• Reach out to people who used to work with the CEO

• Ask the company to share their recent employee pulse surveys (i.e. from Culture Amp, Lattice…)

• Use Whispered’s company insights database

• Whispered’s network with investors and top executives allows us to background check senior executives before you take the position

• Check out their LinkedIn posts and X posts.  Are they actively promoting their business or are they silent?  Are they weighing in on political or social topics and how do you feel about what they are saying?  Regardless of your own politics, if you take a senior role at that company and your CEO is mouthing off about triggering topics, you will be having to manage the fallout.