Leadership Insights

A few insights after several decades of entrepreneurship and leadership.  YMMV.

Never stop recruiting better talent - Place extreme value on recruiting, retaining, motivating, and empowering the best possible business and technology leaders.  Averse to micro-management in favor of empowerment and advocacy.  Finding, attracting, retaining, and motivating the best talent is the most important job of the CEO.   If a team member is not worthy of trust or autonomy, replace them earlier rather than later – for the greater good.

Take exceptional care of our people - so they can take care of our business and our customers.  Make this the company we all want to work for and recommend to others.  Camaraderie, quality of life, friendships at work and culture retain the smartest people, all of whom have other options and choose to work here.  Assume that the competition will only become more aggressive at recruiting our talent and stay ahead by deliberately focusing on culture, motivation, and finding joy in work.  There is more to it than just money, but excellent all-around compensation is a must-win for retaining top talent.

Hybrid work is forever BAU -  and the best talent demands it.  This is no longer a 9-5 M-F world.  Embrace fully technologies like Slack and Zoom which facilitate hybrid, distributed, 24x7 global operations.   Meet regularly in person for workshops, social events, meetings, planning, key customers, etc. but do not burn time commuting or in an office when it is not creating value or by team choice.   Where possible, provide co-working or other onsite options for those who prefer them.  Give smart people the latitude to do their best work. 

Engage personally while avoiding micromanagement - A willingness to go deep when needed, especially when a project or team is challenged or would benefit from more direct involvement.  Trust, verify, and support.  Micromanagement of trusted leadership team members is a last resort and actively avoided except in crisis.

Lead by example, building for permanence - no task or job is “beneath us” and no one is a peon.  Every team member has a key role and should be empowered and trusted to make decisions.  Do not hire technical hero “firefighters,” as they eventually end up becoming near-arsonists - instead focus on building a team that assumes and anticipates turnover, including among senior leadership.  Trust, but verify, and hold people accountable for the decisions you empower them to make.

Focus on a small number of must-win initiatives.  Execs must focus on the few things that no one else can do.  Delegate nearly everything that can be delegated to trusted managers and team members, except for matters relating to product, sales and services process, recruiting, outreach and developing business strategy.  Strong COO, CRO and CFO are at least as important as the CEO, CTO, or any other exec.  Business leadership is a team sport.

Modern Agile methodology = business agility.  Strong preference for transparency, asynchronous / distributed operations, results-oriented work environment (ROWE), investment in automation and systems integration.  Waterfall, at least in tech, is obsolete and the antithesis of business agility – a boat anchor slowing down innovation and frustrating the smartest minds in business.

Actively partner with the world’s best companies.  The world’s most prominent technology companies can be incredibly powerful allies, advocates, and market evangelists.  Build the best GTM and strategic partnerships possible.  Invest heavily in these strategic relationships, and make sure they are consistently seen as a two-way street. 

You can have it done quickly, cheaply, or correctly. Pick two.  Especially in tech.

Better, faster, and/or dramatically cheaper.  If you can't pick two, you are probably wasting your time on the wrong project.  

Stand up for what you know to be right.  Even when it is hard, or expensive, or emotionally draining.  Few people ever live to regret fighting for what they believe in.  Many live with regret for not adhering to their own principles and taking the easy way out.  Integrity matters.  When you know in your heart what is right, follow your instincts and stay true to your values.