Plan for the future

Leadership Moment: Founder’s Syndrome

Founder’s Syndrome occurs when a company founder remains in control for too long. Their approach, which might have been fantastic a decade ago, may no longer be appropriate for the situation that they find themselves in. While they might ostensibly be seeking a successor, what they seem to be looking for is a different version of themself – someone who will make all the same decisions that they would have, but without them having to deal with the long hours.

Organizations often adapt around that founder. “Yes-men” abound, because it isn’t safe for your longevity to disagree with the founder. Problems fester, because people are afraid of tackling them in a way that the founder won’t agree with. Meanwhile, the founder is increasingly frustrated at the few remaining people who obviously won’t get on board.

Last week, Orca Security (a company I work for as their Advisory CISO, and invest in as YL Ventures’ Operating Partner) had a change of CEO. Granted, it’s one founder stepping down, and another stepping in, but I’m really delighted to see a level of maturity in a startup CEO to see an opportunity to establish the next leader of the company, and move early, rather than way too late, to ensure a seamless transition. Companies that don’t plan for their CEO succession will often be left with a crisis, which triggers a CEO departure, with no one available to step into the CEO’s shoes.

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One Minute Pro Tip: Talk about two jobs from now

Performance development conversations with your team can easily go south. You might not think they are ready for a promotion, but they do. When this happens, conversations about what they need to learn to be ready for the next job will turn into arguments.

Talk about two promotions/transfers from now. These conversations are less likely to become fights, and your team members can work on the skills that they will need in small ways, giving them time to develop them well in advance of need – and also identify what career paths they might be less interested in.


Chapter 38 Teaser: Don’t be irreplaceable; be uncloneable.

There’s a certain comfort in knowing that you are irreplaceable. When layoffs happen, you won’t be at the top of the list, but when retention grants show up, you will be. Until one day, out of the blue, you discover that you don’t have a role anymore. What happened?

Every time your leadership met to talk about staff, your name came up, but not in a good way. No one likes irreplaceable team members; every single one of them is a risk to the business. One day, they will depart, leaving the organization high and dry. Every effort to have them train other people to learn to do the work seems to fail, so, at some point, you just bite the bullet as an organization, rip off the bandage, and go cold turkey. It’ll suck for a while – the organization needs to either get rid of systems that no one understands, or throw more bodies at a problem than they should. But in a few years, the organization will be smoothly running again.

A better approach is to aim to replace yourself. Not in everything you do, and not with just one person; you aren’t trying to create a mini-you, after all. What you’re ensuring is that you aren’t a risk to the business by being the only one who can do any specific thing. The value that you bring is in the synergy among all of the things you do. And when you’ve foisted off all of your work onto other people, you can change to a role that you might enjoy better.

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April 11, webinar, host: Creating a Cloud Security Strategy.

April 18, 1% Leadership is released!

April 19, webinar chat: Writing your Cloud Opus: A Deep Dive into Orchestrating your Cloud Security Remediation

At RSAC (times Pacific):

April 24: 10:50 am, Telling Fairy Tales to Your Board

April 24: noon, RSAC bookstore, signing books

April 24: 5-7 pm, Welcome Reception, Orca Booth 527, book giveaway & signing

April 25: 7-9 pm, Orca Security Cocktail Reception

April 26: 2:20-2:35 pm, Bishop Fox Livestream

April 26: 6-9 pm, YL Ventures & Portfolio Companies Reception

May 7-12: Tel Aviv

May 16: panel moderator, Cloud Security Live

Behind the paywall: Predicting unusual things

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