The purpose of this document is to help you understand in greater depth what a headhunter is generally trying to get out of an interview and to give you some hints and tips on the dos and don’ts of what and how you present at that interview.

From a headhunter’s perspective an interview has three dimensions:

  • First and foremost we are trying to work out whether or not you can do the job to our client’s satisfaction.
  • We are taking the time, in person, to present the opportunity and organisation to you, in the hope that we will raise your interest and that you will want to take the process forward.
  • We also, however,  need to extract enough information at an interview, not only to decide whether you are the right candidate to shortlist, but to write a comprehensive and compelling report covering the areas our client is interested in.

Many candidates don’t always take into consideration all the points on this agenda and this manifests itself during the interview in many ways.

What a candidate should bear in mind is that the headhunter is taking decisions on behalf of his/her client by proxy. Some of these decisions are easy: the criteria are black and white. Others revolve around chemistry and preferences. Ultimately we’re simply trying to answer the question “Will our client be impressed by you?” Whether or not you make it to the shortlist depends simply on our interpretation of what you (and referees) tell us and how and whether we think our clients would be delighted to hire you. I do truly believe that all top-level headhunters want the same thing: for our clients to be delighted by their experience of working with us; to think that our process has been thorough and fair and, of course, that ultimately we are presenting outstanding candidates who will deliver significant value to their organisations. Please consider all of these points before you agree to explore an opportunity further at interview: otherwise, you are probably wasting your time. Bear in mind that at the most senior levels in IT, that is at CIO/CDO and top team level, there simply aren’t that many fantastic roles in fantastic organisations paying the right salary levels. If a good one comes up and you have the opportunity to discuss it further, let’s make sure that you at least have the choice of whether to take the role or not.

Before the Interview

Any reputable headhunter will have written a thorough and, hopefully, honest candidate briefing document. It should contain everything that the client believes that you should know at this point. That does not mean that it tells the story in its entirety: some things are simply best not committed to paper. Bear this in mind as you go forward. We are occasionally told things by clients that we could not possibly put in writing but that does not mean they will not affect our decisions and judgment during the recruitment process. Part of any top headhunter’s role is to flush out the covert agendas of our clients and to take them into consideration when recruiting. Clearly, there is no room for arbitrary prejudices (race or sex etc.) similarly, there is no point in interviewing candidates whom clients would simply not employ e.g. it is not uncommon for clients to be prejudiced against people from certain organisations or who a lack a particular experience, regardless of the headhunter’s opinion. If you are not shortlisted for a role, there is always the possibility that there are good reasons which a headhunter is simply not at liberty to disclose.

Having read the candidate briefing document and honed in on key specific challenges, go back over your CV, reflect on your career and think about the areas where they match and identify, for your own purposes, any significant gaps. To arrive at an interview without having studied a company’s website and company report in some detail is foolish. It is vital to be able to demonstrate your understanding of a company’s key challenges for at least the next 12 months. Please bear in mind that we are not simply interested in your ability to do your job but are also trying to gauge your level of interest: are you serious about the move? Are you genuinely interested in exploring this role in greater depth? If you are, invest the time in preparation.

At this point, having done your homework I should be in a position to tell you that you are totally prepared for your interview. Experience tells me however that there is one point that I should mention before you arrive and that is: dress. You might think that at this level it is obvious to all candidates what is or is not acceptable attire for a formal interview, but I could regale you with many amusing stories and so could each and every one of my colleagues. Gentlemen, If in doubt please wear a dark suit, smart shirt, tie, black shoes, and socks. Backpacks are for programmers, not CIOs. Ladies, elegant but professional attire. Ideally, it’s best if we don’t notice what you are wearing. Too much glamour or a poor sense of dress is distracting for an interviewer. Overpowering aftershave or perfume is a no and of course, there is my own personal dislike of too much jewelry, particularly dangly earrings. If you need to attend the interview in casual clothes for any reason, please call in advance and let us know. Finally, if despite all attempts to arrive punctually you know you are going to be late, please call in advance and give a sensible ETA and of course, an apology.

So you arrive:

  • On time
  • Well dressed
  • Well prepared
  • Ticking (more or less) the boxes outlined in the candidate briefing document.

You are now one of probably about 8 to 10 people being invited to interview from dozens (sometimes 100s if the role was advertised in the press). You have a chance to make it to the shortlist, but please remember, of the 8 to 10 I am interviewing, I am still only planning to shortlist about 4. This is where I have to point out that ticking the boxes that you have interpreted from the candidate briefing document gets you if you’re lucky, the interview and no more. You must assume that every candidate being interviewed probably ticks those same boxes.

If I had to choose one single gripe about senior level technology candidates, it’s that they often come across as if we are having a general chat. We are not. If you are dealing with a reputable headhunter, they will, like me, be looking for outstanding candidates. For these top roles ticking the boxes simply isn’t enough. This should be seen as your opportunity to sell yourself, your achievements, your capabilities, and potential. All roles are different and each will have particular requirements in terms of experience, skills and personal attributes. Whilst you are clearly not a mind-reader, at this level you can be fairly sure that a headhunter will want to explore a number of specific areas. Having consulted my two fellow CIO headhunter colleagues, we agreed that the main areas for discussion are likely to be:

  • Strategic vision
  • Leadership
  • Commercial acuity
  • Change
  • Influencing Skills
  • Innovative thinking
  • Relationship and stakeholder management
  • Building partnerships with third parties
  • Sourcing
  • International Experience
  • Judgment
  • Intellect
  • Delivery (often digital)

In any case, to go into an interview not having considered your own expertise in each of these areas would be short-sighted. By the way, we are looking for evidence, not your theoretical opinion on any of those areas.

Headhunters will usually start the discussions by explaining the opportunity and the role in their own words: bringing to life and adding more detail to the candidate briefing document that you have already read. Usually, at this point, you will be offered an opportunity to ask questions. I cannot press upon you strongly enough how bad it looks for a candidate to have none. If you are serious about giving up your current role and taking this life-changing opportunity to move, it is impossible to believe that there is no area you would like to explore further. Equally questions designed to show off are easily spotted and never well received. Be honest and tell us what matters to you, but please only two or three, remember our primary purpose is for us to understand more about you and your capabilities. If you satisfy us on that, you can ask as many questions as you like later.

One of my colleagues always starts the interviews by discussing where a candidate is in his or her life and career and what they want to achieve, the opportunities and impediments and what might attract them about this alternative role. These are all important points to consider before you look at a move. At this point, it is the headhunter’s turn to ask questions, since we have already established that you are not a mind-reader you must be prepared for anything. Listen to the question, put yourself into the headhunter’s shoes and work out quickly what they’re getting at. Take a couple of seconds to think about the best example from your CV (not necessarily the first one that pops into your head) and if necessary ask for clarification on the question and offer a couple of alternative examples. Give the headhunter the opportunity to select the most appropriate. As you answer, check back that you are offering the right level of detail. Most answers need a beginning, a middle and an end. The beginning will be to set the context to briefly describe the situation, the business problem and how you came to be involved. The middle bit covers what you and your team delivered and the challenges you faced. The end bit is the metrics by which you have measured success. If you follow this format, where possible, giving a business context and positioning your achievements in that context you will come across as a commercially astute, results-orientated individual.

Every headhunter will tailor the interview to the role, but probably has a few questions that they always ask. My own favourite revolves around influencing skills but others include mistakes you’ve made and what you’ve learned from them, strengths and weaknesses and almost inevitably an exploration of your leadership skills. It is vital that you can answer the question “What in your opinion makes a great leader?” and hopefully, how you fit that model. Please bear in mind that people management is one simple strand of leadership, but that it also includes:

  • Vision
  • Communication skills
  • Boldness
  • Real self-awareness
  • Real self-confidence
  • Innovation
  • Ability to build an outstanding team
  • Willingness to empower them

As well as many other things that countless authors have written about in their books on leadership. It’s a good idea to read at least one of them.
So finally, having consulted with my colleagues, I would like to put forward our thoughts on some of the obvious dos and don’ts at an interview.


  • Your homework.
  • Understand what motivates you and how this role will help you to get to where you want to be.
  • Be genuinely enthusiastic about what you have done, your company and this opportunity. Passion is always welcome.
  • At least convey a desire to explore this opportunity thoroughly so that you can decide whether it’s for you or not (you may well still have doubts at this point and that’s fine. However, you must at least show that you have a plan that will enable you to make a firm decision).
  • Be able to demonstrate clearly, with evidence, what your major achievements have been and how they have positively impacted on each of the companies you’ve worked for.
  • Maintain eye contact and engage the person opposite you.
  • Be honest. Good headhunters will always take references. If you are lying you will be found out.
  • Recognize that you must give outstanding answers that differentiate you in this highly competitive market. Do your answers pass the ‘so what’ test?
  • Listen carefully to the question, answer that question, the whole question and nothing but the question.
  • Remember to smile. Having gravitas and being professional does not preclude you from showing warmth. The headhunter will want to know that you can build a relationship with his or her clients and being stony-faced for an hour is not a good sign.
  • Understand the question and be concise and precise in your answer.


  • Skimp on preparation. It will come back to haunt you during the interview and worse, could result in you taking a role that simply is not right for you.
  • Have an inflexible agenda that you are determined to get across at all costs, regardless of the question.
  • Lack of self-awareness. Everybody has weaknesses. Not only must you acknowledge them, but we would also like to see evidence of your plans to improve them. A defensive ego is definitely a turnoff.
  • Make stupid comments belittling either the role you are discussing or the company. Headhunters are generally proud to be working for their clients and you will not win favor by slating them.
  • Waffle or make the mistake that we are here for a nice chat.
  • Forget names, titles, figures. Re-read your CV and have the relevant facts at your fingertips. This will facilitate a good interview, enabling you to concentrate on answering the question, rather than stumbling over facts.
  • Give off the wrong signals with your body language. Aim for relaxed but engaged.
  • Forget to ask questions or, even worse, ask stupid questions which convey lack of preparation.

You’re busy, we’re busy. Nobody wants to waste time in an interview that is going nowhere. You can assume, therefore, that the headhunter is probably willing you to succeed, willing you to impress them and willing you to be good enough to shortlist. Any top-level role will probably be accessed only via a fairly tough interview, but on the whole, the aim is not to trip you up but to explore your strengths and weaknesses so that clients have the very best information to judge whether or not you are right for the role and indeed, for their organisation. For the same reason, honesty is the best policy. There are worse things than not getting the role and at the top of that list is being appointed to a role that you are simply not right for. At the end of the day, if this wasn’t the role for you, there is almost certainly a better one around the corner. Armed with this information, you should be prepared to give the best interview you can. Remember, a good interview will deliver a positive impression to the headhunter and it is entirely likely that he or she will contact you in the future about a more appropriate role. I wish you good luck!

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