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Written by Ru Jupp

Digital Leadership Search - A guide to success

Digital Leadership Search - A guide to success

Challenges I’ve faced as a Headhunter and what I’ve learnt

With over two and a half decades in the business of retained executive search for digital C-Level, SVP and VP roles, I’ve certainly faced many challenges, and made a few mistakes in my time. Each one though has been an opportunity to learn, to refine my process and to enhance the service and experience that leads to delighting clients and hiring great people that stick. 

As I reflect, I'm humbled to say that I feel the results speak for themselves. 

As an independent headhunter, with few off-limits, deep expertise and a personal touch I am very proud of the work we have done for clients from blue-chip to SME/Start Up and expect to continue to learn and refine through 2024.

I thought I’d share just some of the  challenges I faced early on, and how I approach them now.


1. Getting the full picture upfront

One of the first hurdles in hiring world class talent can be the misalignment of expectations among client decision-makers. Rarely are all stakeholders aligned when it comes to the ideal candidate and fit.

Take for instance, hiring for a Product leadership position; the Chief Marketing Officer (CMO) and Chief Technology Officer (CTO) will often have disparate views. There will be overlap and but there will also be different requirements in the skillset and type of person. It's therefore imperative that I engage with all decision-makers, understand their perspectives, and respectfully highlight both areas of alignment and divergence; only then can you get everyone on the same page. Failure to do so will almost always result in issues later on, and so being afforded the opportunity to probe deeply is fundamental.

This is a key part of my process. I invest a considerable amount of time listening, absorbing and considering what clients are looking for, sharpening it, challenging it, then playing it back to ensure alignment and clarity. I am always happy to help prospective clients with this exercise before they are ready to hire, as this is typically a major stumbling block. Get in touch directly if you would like help here.

I get some great feedback on how cathartic this experience is, and I love it when I witness clients get really excited about the search and partnership.


2. Scratching below the surface of company culture

To truly understand a client’s company culture, it's crucial to scratch below the surface and the buzzwords. I make a point of speaking to individuals right across the organisation, spanning different functions, departments and regions to glean an authentic view of a company’s culture - crucial in hiring the perfect fit.

Hiring fresh leadership into a business is a great opportunity to enhance a culture. There can sometimes be a chasm between what a business wants its culture to be and what it actually is in practice. Hiring executive leadership should always be a move in the direction the company wants to go, additive to the desired culture, rather than upholding the current.


3. Respecting people’s time and the cadence of a working week

In the rush to meet schedules and deadlines, it's easy to overlook the importance of giving candidates the flexibility to choose interview times that suit them best. A focused and thorough assessment requires the candidate to be at their best, and this might not always align neatly with my diary. 

Striking a balance by accommodating the candidate's preferred time of day and week even if it doesn't align perfectly with my diary, is a small but significant consideration. This is as important to get right when arranging candidates to interview with clients, of course.


4. References, references and more references

Meeting a great candidate can be exhilarating, and enthusiasm can cloud judgement. Hence the importance to take lots of references and look for the balance, the critique and useful insights on the individual. Asking good probing questions, including difficult ones that might unearth a concern or observation is something I used to shy away from in my early days. Not any more.


5. Empowering clients to hire swiftly

After recommending our shortlist after weeks of endeavour it’s often the first or second person our client interviews that they love. This is not something I orchestrate, but is a trend I’ve observed.

While it's essential to respect the client's desire to meet the entire shortlist, it's equally important to recognise when the right fit is evident early on. If the candidate is active and has other serious opportunities they’re considering, we recommend moving fast with the candidate through the 2nd and 3rd stage assessments and being ready to make an offer to that person. 

Advising clients of how much work has gone on to produce a 4-5 person shortlist often from over 250 people considered, and to trust their instincts and move swiftly with a promising candidate can be key to securing top-tier talent, particularly when great talent are actively exploring multiple opportunities. So sharing our progress through every search, keeping communications up and managing clients expectations at every step of the search only increased confidence in the shortlist we ultimately present.


Want to discuss a leadership search or just want some advice?

Drop me a note and let’s discuss.

Get in touch

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