How to pass through the guarded gates & (C) Level up

Tasked with the heaviest make-or-break decisions, being everything to everyone, enduring vast amounts of stress and pressure, embracing and dodging risks, motivating and leading people, first in/last out and all set against a background of constant nay expected, change.  

In  the technology industry your entire business model can be obsolete within weeks due to disruption, competition, scuttlebutt, customer ratings, policy or the subtle game of investment.  Being a tech exec is not for the faint-hearted. Add to that, fronting-up to boards, fronting-up to teams, fronting up to media and the healthy conflict to endure with peers, competitors, suppliers, etc... well you get the picture. Elon Musk’s quote of eating glass whilst staring into the abyss begins to make sense.

There are those people we all know who are (more or less) deserving of being an executive in a technology business. So, how did they get there? To get there is not just doing the right work, in the right business with the right team and at the right time. That part is critical. You must have credibility, expertise and evidence of potential. That is a given. And that is your permission to play.

How do you get the job?  Some get it by starting a business and appoint themselves. But, most must run the gauntlet of judgement to earn the pips. There are a few profiles of people that hold the keys and are often called upon for a variety of reasons to decide who will own that C at the front of their title. More often than not, your chance to become an executive will come down to a single  meeting where you must perform and impress to get the defining first role of your career.

Bouncing these thoughts around here in the office, we wanted to get the different perspectives and expectations from three very different profiles of the decision-making contributing to a C-Level appointment.

Our goal is to help you understand what to expect from this audience so you can be best prepared.


The Investor:

Rudy Bublitz: Co-Founder & Director of Angel Invest crew Flying Kiwi Angels

The Board member/advisor:

Justin Tomlinson: Founder, Advisor & non-exec Director of DeliveryCraft & Propellerhead (among others)

The CEO:

Andrew McPherson: CEO of Experieco & Industry Connect


  1. How would you build your impressions of the person prior to the meeting and what preparation would you expect?

Justin: I actually look for followership. Recommendations particularly; no one recommends someone they don’t genuinely rate as they know it reflects on them. I want someone to know the commercial fundamentals (homework) and to have a desire to be aligned culturally.

Rudi: I don’t do prep before a meeting, want to hear it from the horse’s mouth. That puts a lot of emphasis on their ability to articulate what they are about verbally.

Andrew:  I would look at any online activity they have; Industry involvement, social media, articles and contribution to the community.  I would also ask around my network to see who knows them and what their impressions were, their history, their relationships. It is important to get an understanding of their approach and mindset; what they are motivated by and what they have done previously.


  1. Which attributes must they display in the meeting that will convince you they are a great leader?

Justin: Being themselves, with skill and I ask what they think motivates people. I’m looking for evolved thinking on drive, a la Dan Pink.

Rudi: Passion aka self-driven, team player and coachable.

Andrew:  Leadership is essentially about achieving outcomes through others.  They need to display authentic relationship and interpersonal skills. They need to have maturity as a leader; have an understanding beyond the superficial skills of leading self, leading others and leading change.  A focus on results combined with an empathy for others.


  1. How would you determine that the skills, experience and pedigree that this person brings is matched with the current stage in the firm’s lifecycle?

Justin: Personally, I’m looking for people who can be progressive and pragmatic depending on what is called for. Pragmatic on compromise from radical ideals and progressive in moving us in the right direction.

Rudi: I’d be looking for metrics just below are the required level, this would be a combination of revenue, process metrics and headcount.

Andrew: I believe change and disruption are constant regardless of the firm’s stage. There is an ongoing need to innovate and improve, to try new things while managing the associated risk.  They need to demonstrate a desire to innovate combined with a structured approach to execution.


  1. The modern C-Level leader must have high IQ, EQ and AQ (or even SQ).  How would you identify these capabilities? Are any of these more important in making a decision on fit?

Justin: Really, you can’t do this in a meeting and people have learnt to say the right things. On the job and through feedback is the best way to test these things, that said, they are utterly critical. Accepting that one meeting isn’t enough is fine by me.

Rudi: Drive comes from a strong vision or purpose (SQ), to grow you need to attract and retain a team (EQ), to be coachable means accepting mistakes and learning from them (AQ), all that has be turned into successful execution (IQ).

Andrew:  These attributes are very difficult to discern from a single meeting.  I believe that you need to have several meetings in multiple situations, both business and social, to observe behaviour and understand the motivation.  I have often invited a candidate and their partner out to dinner with my wife and I to get a better understanding of the person. I believe that IQ, EQ, AQ & SQ combine to create the overall fit in addition to attitude and motivation.


  1. No leader is an island.  How important is the richness and depth of their relationships and network to the person’s success in a C-level role?  How would you ratify this?

Justin: In technology this one is more tricky. High technical competence and introversion appear to correlate. That said technical peer networks tend to be very strong. I look for skills in situation sensing and self awareness. (e.g. know’s when to stop talking and that they have certain “features” which also have “benefits”).

Rudi: Good networks help to widen horizons, validate hypotheses, sequester resources. network also validates an individual’s standing.

Andrew:  As a leader, relationships are everything.  Enduring relationships beyond the superficial friendships or workplace colleagues are a great indicator of the ability to establish and maintain relationships through ups and downs.


  1. For you, what are the indicators of a person’s historic/indicative success in a C-Level role?  What evidence do you require of this?

Justin: Again, I look for followership and also I have to say that being responsible for massively scaled household name things goes a long way. Indicative success can be seen in potential, i.e. a real reason why this person is being held in a certain role owing to poor succession planning or just circumstance.

Rudi: Angel investing is all about growth, so I’m looking for evidence of growth in their previous roles, revenue, process metrics and headcount.

Andrew:  I think it is important to see a pattern of taking on challenges and the resulting growth, particularly in a time of change.  It is about how they apply themselves. Leadership is a choice. They need to demonstrate that they have been taking leadership opportunities and are realistic about the impact they had; what went well, what didn’t and what they learnt!.


  1. What are the hallmarks of a future C-level leader?  And how would you identify this?

Justin: People focus over subject matter, control over need to react, experience in a fiery hot cauldron and the resilience to have thrived.

Rudi: We like to think that we can recognise them when we see them. Most important hallmark is their willingness and ability to keep learning.

Andrew:  Continual learning, continuous improvement and continuously exercising the leadership ‘muscle’.


  1. What would you expect people to do post-meeting?  What kind of follow-up is the right amount?

Justin: Eloquent brief summation and at least two things I hadn’t thought of would delight me.

Rudi: Clarify next steps and timelines, when they pass without action follow-up by email. Respond with references and other documents if requested promptly.

Andrew:  I would definitely expect an email follow-up.  It should be thoughtful and well written, highlighting any key insights, considerations or areas where we made a connection.


The preparation and planning required to be able to satisfy the expectations outlined in our interviews is not arduous, though it should be carefully executed as each position will be different. Like anything in senior leadership the level of preparation and planning will be one of the biggest  indications of the performance.

Finally, the ability to know, understand and manage your self is equally as important as the ability to do so for others. Aptitude is important, but equally is the quantifiable evidence of abilities. Leadership is many things to many people, but the the ability to articulate and demonstrate the authentic principles that are most important to the hopeful candidate to this audience will ensure the highest chance of a good fit and success in securing the right role.