Your IT Leadership Questions Answered: This Month's Most Critical Hiring Dilemmas Solved

THIS MONTH'S CRITICAL QUESTIONS

"We've been trying to hire a CISO for six months with no success. What are we doing wrong?"

This is perhaps the most common question we've received this month, and for good reason. The CISO talent pool remains exceptionally tight, with demand far outstripping supply.

✔️ The real issue: Most organisations are approaching CISO hiring with outdated expectations. Our experience over the past 12 months of recruiting shows that most CISO job specifications demand a combination of skills, experience, and credentials that fewer than 50 individuals in the UK currently possess.

✔️ The solution: Consider a tier-based approach:

Fractional CISO: Bring in a seasoned security executive 2-3 days per week to establish your security foundation and mentor internal talent
Clear succession planning: Identify and develop internal talent who could grow into the CISO role within 18-24 months
Realistic market expectations: Be prepared to pay 15-20% above your initial budget or consider candidates with adjacent experience (privacy leadership, risk management) who can grow into the role

One of our network recently solved this dilemma by hiring a fractional CISO for a 9-month engagement while simultaneously bringing on a Director of Security Operations with CISO potential. The fractional leader is now mentoring the Director, with a clear transition plan in place.

"Should we prioritise technical depth or business acumen when hiring a CTO?"

The eternal question - and one that reveals more about your organisation's needs than you might realise.

✔️ The context matters: Your current growth stage should dictate this decision:

Startup/Scale-up phase: Technical depth usually takes precedence, as architectural decisions made now will impact your ability to scale later
Growth/Expansion phase: The balance shifts toward business acumen, as technology decisions become increasingly tied to commercial outcomes
Enterprise/Transformation phase: Business acumen typically becomes the dominant requirement, with technical depth needed primarily for credibility with the engineering organisation

✔️ Our recommendation: Rather than seeing this as an either/or decision, consider your specific technology challenges:

If you're facing fundamental architectural challenges, prioritise technical depth
If you're struggling with aligning technology and business objectives, prioritise business acumen
In most cases, the ideal solution is a technically-credible leader with strong business sense plus a technically exceptional deputy who can drive implementation

"How do we attract technology leaders from major tech companies to our non-tech organisation?"

This question reflects an increasingly common challenge as every company becomes a technology company.

✔️ The misconception: Many organisations believe compensation is the primary barrier. While important, our exit interviews with tech leaders show that scope of impact, access to emerging tech and autonomy consistently rank higher at the senior level.

✔️ The approach that works:

Sell the problem, not the company: Technology leaders want to solve meaningful problems. Be transparent about your challenges and the impact solving them will have
Guarantee autonomy: Define clear areas where the leader will have decision-making authority - this is often more valuable than a higher salary
Create visibility: Ensure the role has direct access to the board and executive team
Offer equity or outcome-based incentives: Link compensation to the value they create

"When is the right time to hire our first dedicated Head of Engineering / IT Director?"

This timing question has become increasingly common as growing businesses reach technology inflection points.

✔️ The signals it's time:

You're making technology decisions that will have 3+ year implications
Technology problems are consuming more than 15% of your SLT's time
You're planning significant technology investment (>£250,000)
You've experienced a security incident or compliance challenge
Your technical team has grown beyond 8-10 people without clear leadership

✔️ Our framework: The decision typically hinges on three factors:

Complexity: How many systems and integrations do you manage?
Criticality: How dependent is your business on technology?
Growth trajectory: How quickly are you scaling?

We recently working with an organisation to place a Head of Engineering, a leader to look review their tech stack, manage team performance, collaborate with the executives and drive engineering excellence. After just 2 months, the founder as seen a boost in morale, output and has a relationship with an expert who can translate technical direction and business needs.

TREND SPOTLIGHT: THE RISE OF THE PORTFOLIO TECHNOLOGY EXECUTIVE

We're seeing a significant shift in how senior technology leaders structure their careers. The traditional one-company career path is giving way to portfolio careers where leaders might simultaneously:

✔️ Serve as a fractional CIO/CTO/CISO for 2-3 organisations ✔️ Hold advisory board positions ✔️ Lead specific transformation initiatives ✔️ Mentor emerging technology leaders

This shift benefits both executives (who gain diverse experience and better work-life balance) and organisations (who access experienced leadership without the full-time price tag).

In the past 12 months, we've seen a huge rise in requests for fractional technology leadership - a trend we expect to accelerate through 2025.

CONNECT WITH US

Have a pressing IT leadership hiring question? Email us at enquiry@lhwpartners.com or connect with Lauren Watkins on LinkedIn.

Looking for strategic technology leadership? LHW Partners specialises in connecting organisations with transformative technology and security leaders, both permanent and interim, email us at enquiry@lhwpartners.com or reach out to Lauren Watkins

Issue #23

LHW Partners: Tech Leadership Loop