5 Things Technology Leaders Want to Know About Your Opportunity
Originally published 2017. Revised and updated.
We’ve interviewed thousands of Tech, Data and Digital leaders over the years. And no matter how senior or specialist the role, we’re still asked a variation of the same handful of questions.
What’s interesting is how rarely these questions are answered properly at the first point of contact with a potential candidate (if at all).
Clarity at the start of the process helps everyone. You’re able to…
Set the right expectations - with both candidates and your internal team
Hook the right people (“you never get a second chance to make a first impression”)
Increase your chances of engaging a great tech leader
And finding the right tech leader can be the difference between value multiplied and value lost.
When this is done well, everyone involved in your recruitment process is aligned. So, when hiring a tech leader, can you answer questions like the following?
1. What are you trying to achieve - and how does this appointment create value?
There are many variants on this question that centre around company vision, strategy, and objectives; and how you’d like technology to contribute.
Does the business know what it wants to be? What’s the role of technology in getting there? Why are you investing in this appointment now? And what would ‘good’ look like, six, twelve, or eighteen months in?
Answers to these questions don’t just help candidates decide whether they’re interested. They signal organisational clarity and maturity. And give the best people a reason to engage.
2. How is the existing tech function perceived by the wider business?
This gives the candidate a sense of where they would be starting from - culturally, reputationally, and politically.
Is the technology team respected and trusted?
Are there legacy perceptions, internal tensions, or bridges to rebuild?
What are their internal customers saying, and what does the business expect from tech today?
The perception isn’t always negative - the function might be thriving. In that case, it’s about maintaining what works whilst adding value elsewhere.
But either way, the best candidates want the lay of the land. Because how they’ll be received on day one affects how quickly they can make an impact.
3. What level of financial backing will they receive, and what’s the appetite for investing in tech?
This is always an interesting conversation. Tech leaders and CEOs/CFOs are often poles apart in their expectations here. At least at first.
As a middle-man, I see both sides. And often hear each side give the other a bad rep when it comes to anticipated spend (or is it investment…?).
But think about your own role. If you’re accountable for something, knowing the resources available to you is a basic requirement.
It could be that there’s limited spend and the candidate will need to create efficiencies to reinvest. Or perhaps you’ve secured funding and they have a war chest.
Neither is better than the other. Candidates just want to know what they’re working with.
4. How influential will this role be?
We’ve discussed financial backing, now what about backing and support in every other sense?
The incoming leader will be expected to make progress quickly. And to do so, they’ll have to make some big, impactful calls. Yet, even the best leaders are only effective when they’re set up for success - when they have access to the right people and processes to influence change.
How are decisions made? Will they have direct access to decision-makers? Will they have the agency to shape outcomes? Will they be on the exec team?
These are crucial questions that will help the right candidates to lean in, and the wrong ones to self-select out.
5. How did this position come about?
Obvious, right?
And yet, few job ads make explicit reference to this. And it’s often skipped over in early-stage conversations.
You might be creating a new CTO role following investment. You might be replacing someone who hasn’t worked out. You might be re-scoping a role to reflect changing priorities.
Each of these backstories drives its own set of priorities on day one. The best candidates know this and appreciate transparency.
Again, there isn’t a preferred answer - just an answer.
In Summary
Hiring a senior technology leader is one of the most important decisions a business can make. It’s also one of the most nuanced.
By clearly answering these five questions, you dramatically increase your chances of engaging the right people and aligning your team around a successful hire.
At Laudale, we help our clients define the role, shape the narrative, and run a process that attracts leaders capable of driving real value.