I started my career in technology in the early 1990s. The internet was nascent. Cloud computing didn't exist. AI was an academic curiosity. Across three decades, every major technology trend has arrived, peaked, and been replaced by the next one. The people challenges - hiring, motivating, leading, letting go - are exactly the same today as they were in 1993.
What You Need to Know
- Technology is the easy part. People are the hard part. Every company problem I've encountered ultimately traced back to a people problem - wrong hire, unclear accountability, avoided conversation, misaligned incentives
- The most important hire you make is your first senior leader who isn't you. Get this right and the company scales. Get it wrong and you'll spend two years recovering
- Culture isn't what you say. It's what you tolerate. Every time you let substandard behaviour slide because someone is technically brilliant, you've defined your culture
- The hardest leadership skill isn't making decisions. It's having difficult conversations promptly and directly
89%
of executives cite people-related challenges - not technology or market factors - as the primary barrier to organisational performance
Source: Deloitte, Global Human Capital Trends Report, 2025
The Constant Underneath the Change
When I look back at Sealcorp, Flintfox, eWatch, and the various boards and investments I've been involved with, the technology stories are all different. Supply chain management. Intelligent pricing. Security technology. Each had its own technical challenges, market dynamics, and competitive landscape.
But strip away the technology, and the challenges were identical.
How do you hire people who are better than you at their job and then actually let them do it? How do you build a culture that sustains performance when the founder isn't in the room? How do you give honest feedback to someone you respect? How do you let go of a talented person who's destroying team dynamics?
I haven't found a technology platform that solves any of these problems. I have found a few principles that consistently help.
Hire Slowly at the Top
I've made hundreds of hiring decisions. The ones that went badly almost always shared a characteristic: I was in a hurry. A role was critical. The pipeline was thin. Someone was good enough. I made the offer because the gap was painful and the candidate was available.
The cost of a wrong senior hire is extraordinary. Not just the direct cost of severance and recruiting, but the opportunity cost. A misaligned senior leader makes hundreds of small decisions that take the company off course. By the time the misalignment is obvious, eighteen months have passed and the accumulated impact is enormous.
At Flintfox, my best hires were people I'd known for years before bringing them on. My worst were people I'd met twice and hired on the strength of an impressive CV and a persuasive interview.
The Interview Problem
Interviews are terrible predictors of performance. They measure presentation skills and self-awareness, not the ability to do the job. The most effective evaluation method I've found is working with someone on a small project before making a commitment. Not as a test - as a genuine collaboration. You learn more about someone in two weeks of real work than in ten hours of interviews.
In thirty years, I've never regretted taking an extra month to find the right person. I've regretted every time I hired fast because the gap felt urgent. The gap is always less costly than the wrong hire.
Mike Ridgway
Technology Growth Advisory
Have the Conversation
The most consistent failure of leadership I've witnessed - in myself and in others - is avoiding difficult conversations. The underperforming team member who everyone knows isn't cutting it. The cultural misfit who's technically excellent but corrosive to the team. The co-founder relationship that's no longer working.
In every case, the leadership team knows the conversation is needed. In every case, they delay. The reasons are always sympathetic: "They're going through a tough time." "We'll give them one more quarter." "It's not the right moment."
There is never a right moment for a difficult conversation. There is only the cost of delay, which compounds daily.
The leaders I respect most share a common trait: they have difficult conversations promptly, directly, and with genuine care for the other person. Not cold. Not brutal. But honest and timely.
Culture Is What You Tolerate
Every company says they value integrity, teamwork, and excellence. Very few actually enforce those values when it's costly to do so.
Culture is not your values statement. Culture is what happens when a top performer behaves badly. Culture is whether the CEO follows the same rules as everyone else. Culture is what gets rewarded and what gets ignored.
At one company I chaired, we had an exceptional salesperson who was consistently disrespectful to the operations team. He hit his targets every quarter. He also created a toxic environment that led three good operations people to leave within six months.
The CEO was reluctant to act because of the revenue risk. We acted anyway. The short-term revenue impact was real. The long-term cultural impact was transformative. The remaining team saw that performance didn't excuse behaviour. Retention improved. Collaboration improved. Within a year, we'd more than recovered the revenue.
5x
the cost of replacing a senior employee compared to investing in retention and development - yet most companies underinvest in keeping their best people
Source: Gallup, State of the Global Workplace Report, 2025
The Leadership Paradox
The further I've progressed in my career, the less I've needed to know about technology and the more I've needed to understand about people. As a young manager at Sealcorp, I succeeded because I understood our products and our market. As a chairman, I succeed - when I succeed - because I understand the people around the table.
The paradox of leading technology companies is that the technology is the least important thing a leader needs to understand. Markets shift. Platforms change. Architectures evolve. What doesn't change is the need for:
Clarity. People perform best when they understand what's expected, why it matters, and how success is measured. Ambiguity is the enemy of performance.
Honesty. People don't need to be told everything. They do need to be told the truth about what they are told. Trust, once broken, is nearly impossible to rebuild.
Space. The best people I've hired wanted to be led, not managed. They wanted direction and then room to figure out how to get there. Micromanagement is the surest way to lose your best talent.
Recognition. Not awards ceremonies and employee-of-the-month programmes. Simple, direct acknowledgement when someone does good work. It costs nothing and it matters enormously.
The One Thing I'd Change
If I could go back to 1993 and give myself one piece of advice, it would be this: invest more time in people and less time in everything else. Every hour I spent on strategy, technology evaluation, market analysis, and operational improvement would have been more valuable spent hiring better, developing people further, and having the conversations I was avoiding.
The technology built the products. The people built the companies.