The more senior the employee, the greater their overall effect on a business; hiring for senior positions is thus more difficulty and comes with greater risk. Senior roles usually (not always) require a large amount of relevant experience, and always require a  particular set of skills, attributes or attitudes. Opportunities for on-the-job training are likely to be slight, and business-need high from the outset. Senior roles also come with senior salaries; expenditure on a candidate that proves to be the wrong choice represents significant wastage.

In short, companies need to get it exactly right the first time.

We’ve created the following guide to interviewing for senior roles based on the executive search observations of our Founder and Talent Specialists, as well as our day-to-day experiences connecting businesses with senior professionals at Juggle.      
We recommend at least six key stages. If that sounds onerous or unnecessary we’d caution you to think about what’s actually at stake here. It’s crucial that you find the right person for your business, and while you may feel under pressure to fill the role, the consequences for selecting the wrong candidate are too severe to allow your current needs - however acute - to dictate the pace. Hire in haste, repent at leisure. 

 This process focuses on interviewing. We’re assuming that you’ve put the time in creating a robust job spec or mission/outcomes/competencies (MOC) document so you know what you’re hiring for, what the candidate needs to be able to do and what you expect them to achieve within a discussed timeframe.


Step 1: “The values test” (telephone/video call)

Step 2: “Real talk” (in-house conversation with you and perhaps a colleague)

Step 3: “When did you last…” (competencies)

Step 4: “You have one hour” (skills test)

Step 5/6: “I’d like you to meet…” (interview with board member/investor/senior team member)

Step 6/6: “Everyone, this is…” (social with the team)

Overall notes on the process

Each section finishes with a summary so you can quickly re-familiarise yourself with the content.





Step 1: “The values test” (telephone/video call)

Once you’ve identified a potential candidate it’s important that you get off to the right start. A simple and comparatively brief (we’d recommend trying to keep it to 30 minutes) telephone or video call can answer most of the cultural or contextual questions you might have about a candidate. Getting these answered as early as possible is important because discovering a cultural mismatch or contextual problem in the middle of the interview process is a huge waste of time and resources.

So before you get into the nitty-gritty of previous experience and technical skills, now is the time to discover: what motivates them and what motivates you? What do you both consider important? Do their goals fit with your mission? This isn’t a CV run-through, this is where you learn about their values. 

You’ll note that all of those questions relate to your business as well as the candidate and that’s important. If you cannot answer them you aren’t ready to have conversations on the subject and you may not be ready to hire at all. We’ll run through what you should be trying to find out and why it’s important you do so.

  • Who are they? The right candidate should be able to put up an answer to this without significant struggle. Regardless of the specific role, a senior professional should be able to superficially articulate their history, talents, goals and needs. If they can’t do it to you, they won’t be able to to do it to their colleagues and subordinates. This is also your chance to identify any glaring cultural mismatches.

  • Who are you? This is your chance to tell them a bit about the company and sell the role to them. We’d recommend doing so honestly, because most senior professionals can recognise bullsh*t (normally they’ve had a career’s worth of practice).  Describe your own journey to join (or lead) the company, and why you’re excited about it. The aim is to get them excited about the role in turn. If you can’t do that we’d recommend thinking again about the job spec. If you can’t get people enthused about the role then perhaps something about the role has to change.

  • Why are you hiring and how will they fit that need? Describing why you are hiring and what your needs are provides important context so that when you ask “How do you think you’ll fit into that? / What do you think you can bring to this role?” etc they know enough to give a concise answer: one that’s more representative and easier to analyse.  

  • What’s important to them in their next role? We’d recommend using this exact phrasing or something close to it, because how you ask this question is important. Asking what’s important to them encourages them to think about priorities, which is revealing both professionally and personally. At this stage you’re only out to listen, not judge. Keep asking questions to make sure you’ve drilled down as deep as you need. A simple “anything else?” is enough to prompt clarification or a new thought.

  • What’s their life like? There’s no need to ask anything specific or personal (and there are areas you should completely stay away from). But getting a basic picture of their circumstances might avoid any issues down the line. Does the timescale you have in mind for filling this role fit with their own needs, for example? Is their current salary within your funding window for the role? Would their location provide a hard barrier? Do they have flexible work expectations or needs that you can fulfil?

Active listening will help you throughout the hiring process, so this is a great opportunity to begin practicing it.

When it’s time to end the call simply say something like “Let’s reflect on this”, then ask them to come back to you if they have any questions. Putting the ball back in their court is useful because it encourages them to do exactly what you’re about to do - think hard about the role and what happens next. 

If you already know that they’re not right for the role then realistically now is the time to say so, but after 30 minutes of probably quite intense conversation it’s understandable if you’d prefer not to. 

In either case, set a deadline as to when you’ll call them back (we suggest 24 hours) and then stick to it. Leaving a candidate you’re positive about to wait with no explanation will probably (and quite rightly) turn them off your opportunity. If you’ve decided not to move on with a candidate then it’s common courtesy to let them know, and slows down your process not to get the job done, no matter how much you might dislike doing it. If you’re interviewing an appropriate number of candidates then you’re going to be saying “no” a lot. You may as well get comfortable with it.


  • Use the phone call to test their values and see if they match your culture.

  • Use the opportunity to sell the role to them.

  • Try to get a basic understanding of their out-of-work needs.

  • Use active listening to maximise the information you get.



Step 2: “Real talk” (in-house conversation with you and perhaps a colleague)


You to them

This is your CV run-through, and it’s important to be diligent and thorough with it. You’re aiming to get a sense of their career in general - including their trajectory - so you’ll have to start at the very beginning. 

If you find going through the very earliest parts of someone’s career boring then our advice is: suck it up. They’re called formative years for a reason. Senior professionals are likely to be in their thirties or older, but in most cases a professional’s career is defined by what they did in their 20s. It’s when the path they’re currently on began, and where the jobs they chose had the most effect on the overall direction of their career. Be diligent and comprehensive when discussing every step of that journey. You’re looking for milestones and key developments, events that had a serious effect on how they feel about work, how they approach their job day-to-day and what they want from their working life. 

These key events might be positive changes or moments of success and reward, but they are just as likely to be negative outcomes, instances of failure. Most candidates will be understandably reluctant to bring these up without prompting, so it’s part of your job during this step to uncover them. It shouldn’t be an interrogation, but you should encourage you candidate to talk openly about everything of note that’s happened to them at work, and failure will be a large part of that. 

A candidate that genuinely professes not to have suffered any professional setbacks may be telling the truth, or may simply lack the awareness to have identified those setbacks at the time. Either of these scenarios is an issue, because if a candidate has never struggled at work then you have no way to determine what they’ll do when placed outside of their comfort zone. You’re looking for someone who is self-aware and honest enough to recognise failure, is thoughtful and determined enough to have already analysed why failure occurred, and driven enough to have already settled on a plan to deal with a similar situation in future. If a candidate appears to lack any of these attributes then think seriously about whether the role might place them in a situation that their experience simply hasn't prepared them for. 


Them to you

This stage should be be reciprocal: this is the candidate’s chance to interview you about the role and company culture in general. The next steps will be more tightly focused and technical, so it’s important to answer most or all of their questions now. As with Step 1, there’s no point progressing with a derailing cultural issue waiting down the track. Be honest and upfront with your answers; don’t obfuscate or dissemble. If you’re conducting this interview with a colleague present make sure they contribute to this stage or allow the candidate time to ask them questions - you’re trying to provide a more complete picture of the company so they candidate can be sure this is a place they want to work. This cannot be overstated - company culture is one of the principal factors in attracting senior hires.

 Now is also the time to get a rough understanding of the type of compensation package that’s expected. This can be discussed and negotiated at length further down the road, but you should at least walk away with an understanding of what their general expectations are and any particular sticking points/specific needs they have. Remember - what they used to earn isn’t important. Use what you think the role is worth to orientate how you think about salary.


  • Start at the very beginning of their career and evaluate their decisions from the start.

  • Press them to discuss their failures or missteps

  • Be honest about your business culture, encourage them to ask questions and determine if you’re a cultural fit.

  • Get a very rough understanding of their compensation/flexibility needs.




Step 3: “When did you last…” (competencies) 

This is the most valuable stage in the interview process and should also be the longest, we suggest allowing at least 90 mins / 2hrs. This step is closest to the formal “traditional interview”. Your aim during this segment is to discover exactly how the candidate does their job - and therefore how they are likely to perform for you. 

It’s vital that you create a realistic list of core competencies based on priority to the business. If you’re hiring for a role outside your vertical then make sure these competencies have been vetted by an expert. Make sure you have a good understanding of what’s a deal-breaker and what isn’t. Expecting to find a candidate that effortlessly demonstrates every competency on your list is unrealistic, and a distraction from potentially valuable candidates who meet most of your priorities and could be an excellent placement with just a small amount of development.


“Keeping a critical position open for months while searching for the “perfect” candidate can result in frustration for the company and lead to potentially negative reaction in the market. Being realistic at the outset and setting meaningful priorities will result in a strong initial pool of candidates, one of whom will make an excellent placement.” - (Spencer Stuart Executive Search & Leadership Consulting)


Create a list of questions before you begin, making sure to include a mix of open questions and direct/closed questions. In this context we’re using open questions to mean those that require thought and a more complex answer, and direct/closed to questions to be those that are answered with a simple, potentially one word answer like yes or no. Don’t feel you have to stick to “standards.” Think outside the interviewing box; the more contextual your questions are the better.


Open questions:

How are you finding…

How would you begin…

Tell me  about a time when...

Open questions - and the follow-ups - will take up about 80/90% of the conversation time. 


Direct questions:

Can you…

Have you ever…

Where did you…

Direct questions may be simple but that doesn’t mean they’re easy. Remembering or coming to the right answer may still take the candidate some time, so try not to overuse direct questions.

These two types of questions should feed in to one another. Direct questions create opportunities for follow-up open questions (and can put people under necessary pressure/push for specific details), and open questions will generate specific enquiries that can be satisfied by multiple direct questions. For example:

  1. Do you have any experience implementing cloud-based accounting systems? (direct).

  2. When did you last implement a cloud-based system, what was the goal and what challenges did you face while doing so? (open)

  3. Do you have a particular system your prefer or have more experience with? (direct)

  4. What do you like and dislike about that system? (open)

It absolutely does not matter if you don’t get through all the questions in the interview. What does matter is that you follow up on each one as you ask it, making sure you’re getting the most complete picture of their competencies as possible. Be assiduous and painstaking in your follow-ups. If it feels like a grilling it’s because that’s exactly what is is; the questions should be challenging for the candidate. Letting them glide through with simple enquiries and no further explanation benefits nobody. 

If you’re conducting this interview with a colleague, now might be the time to adopt different strategies between you. Joint questioning (more commonly known as good cop/bad cop) can be an effective method not because of some unsettling psychological effect - this is still an interview, not an interrogation - but because it both challenges the candidate to formulate and explain two different types of answers AND allows the two interviewers to each focus on a specific style and manner of questioning. Whatever you decide to do, make sure the third party in the interview is adding value (looking for details, clarifying, making sure nothing is missed) rather than distracting or muddling the situation (repeating questions, straying off-topic etc).

Remember to maintain active listening throughout - it really will help you get more from the candidate and remember more of what’s discussed, allowing you to make a better-informed decision when you revisit the interview later.

Leave some time for questions at the end (15 minutes of 90 minutes or 30 minutes out of 2 hours). This is an important step as it allows the candidate to revisit and clarify anything they think is important (which could furnish you with a vital bit of information or clear up a misunderstanding). 


  • Use closed and open questions to determine their core competencies.

  • Follow up, follow up, follow up.

  • Don’t search for the “perfect” candidate - focus on what they can do and determine ahead of time what is a dealbreaker and what isn’t.

  • If you’re interviewing with a colleague make sure you strategize between the two of you.



Step 4: “You have one hour” (skills test)


“We believe that you can assess some things in an interview format, but that there are many areas that you can’t. Interviews... are not nearly as valuable as passing the range of tests we’ve devised as part of the hiring process.” - Kieran O’Neill (Thread)


A technical skills test can be a valuable part of the process, even for senior professionals. In our experience, lots of professionals will actually drop out at this stage, either because they struggle with the test or because they dislike being put on the spot in this manner. We can only advise, but our suggestion is that someone who is too hesitant or dismissive to demonstrate their skills when asked is not the right fit for your business. They will be asked to use these skills every day once they are through the door: what exactly is the issue with being asked to demonstrate them before that happens?

You will almost certainly need to get an outside advisor for this step, in order to set up a relevant and competent test/put them through their paces. They should be an expert, someone who uses these skills every day. 

Creating the test will be more straightforward for some roles than others. A technical role or any that uses particular tools should be simple enough (you don’t need to reinvent the wheel). 

Non-technical roles may require more planning. It might be useful to focus on the act of creating something: a deck, a script, a strategy. Take something that the role requires and ask them to make it under timed conditions, but make sure that your exercise is general enough to be manageable for candidates that don’t have your business context:

“Even if you ask them to brainstorm for hours, keep in mind the inputs into the process—they only know the specifics you have provided them. For example, don’t expect a marketing candidate to magically come up with the right pricing strategy for your product without a chance to really dive in.” - Steven Sinofsky (Andreeson Horowitz)


You may decide to use a member of the team that the senior hire will be working with or be responsible for as your expert. This is perfectly fine and practical, but we recommend you consider the following:

  • Explain to the team member why they have been chosen to formulate the test. Be honest and leave no room for ambiguity.

  • Double check the test and, if the team member will be present with the candidate at any point, their own interview style. It’s very possible that they have never been involved in interviewing someone before; give as much guidance as you think is necessary.

  • Make sure you avoid politicising the process. Is the team member someone who might consider the role themselves at some point? How closely will the two parties work together if the candidate is successful? It’s important that the candidate cannot make any assumption of impropriety. 

A note on specifically “take-home” exercises - in our experience these are better for mid-level roles. A senior level candidate can probably succeed at any exercise when given a large amount of time and resources (which you will be unable to measure with a take-home). It’s not so much a case of whether they do well in the task as whether they work confidently, practically and creatively - something you’ll only be able to determine if they set to the task in front of you. We recommend asking them to do it in-house.

The perfect take-home exercises for senior roles doubtless exist, but we’ve never really been able to make it work. We remain to be convinced, but that doesn’t mean we couldn’t be: if you think you’ve found a senior level take-home exercise that’s truly useful then we’d be very interested to hear about it. Send it to us at and we’ll take a look.

If you’re considering moving onto the next stages, we assume it’s going well. Now is a good time to check back in with all parties. Does this still work for everyone? Are things progressing to the previously discussed timescale or do you need to make some changes? Although you don’t need to discuss this further with the candidate, now is the time to make sure you have their individual compensation package - salary, benefits, flexible working requirements etc - worked out and squared away; that includes the initial offer and the window inside which you’re prepared to negotiate.



  • Tests and exercise can be useful even for senior roles.

  • Get an expert to help you design the test and be prepared to update it if business context changes.

  • Don’t set exercises that require knowledge of your business goals or status.

  • “Take-home” tests are less effective for very senior roles, consider asking them to do the exercise in-house during an interview.




The next two steps don’t need to happen in sequence; we leave it up to you to decide which occurs first.


Step 5/6: “I’d like you to meet…” (interview with board member/investor/senior team member)

One final meeting accompanied by someone in the business that you respect - and someone weighty enough to really sell the business to the candidate. This could be a board member, investor, CEO or team lead. Tailor the specific person to the candidate: if they’ve got this far then you must be thinking about closing this deal, so it’s worthwhile choosing  a person that’s likely to make a positive impression and have a serious effect on them.

It’s important to remember that you are still the decision maker. By all means value your senior colleague’s advice, but don’t be tempted to defer to them this late in the process just because they have a lead role in the business. You’ve done the research, the work and the conversation up to this point. Trust your own judgement.


  • Value your senior colleague’s opinion but trust your own judgment and the work you’ve put in.


Step 6/6: “Everyone, this is…” (social with the team)

There’s no harm in getting the team involved earlier in the process if you wish, but a note of caution: avoid becoming over-collaborative. It is neither feasible nor appropriate that decisions like this be made by anyone other than yourself or the hiring committee. Your team have other priorities (and you have a level of overall awareness that they don’t). 

This should be a social event, but avoid relying on the social effects of alcohol; check in advance if your candidate drinks at all and, even if they do, make sure the event doesn’t become too raucous. We hope this goes without saying but at no point should anyone feel pressured to imbibe. There are plenty of other social gatherings you can set up that don’t revolve around drinking. 

It’s very possible that you have multiple candidates reach this stage and that the final choice is dependent on their own needs, timescales or reactions to the compensation offer. If these are your circumstances consider postponing this step until you’ve reached clarity on the issue. Having the team meet multiple potential senior figures is stressful and invites politicking. 

To use an analogy that’s at least tonally accurate: this is like the first meeting between a new partner and your children: you want it to go well, and you don’t do it till your serious. Multiple candidates would be simply too stressful for your kids, so don’t inflict them on your colleagues. 


  • Don’t involve your team until you’re close to closing the deal.

  • Don’t make the event too boozy.


Overall notes on the process

Better too many than too few. 

Although intensive interviewing can be exhausting, meeting with as many worthwhile candidates as is feasible is the most efficient strategy for a variety of reasons. Conducting multiple interviews within a short window allows you to contrast candidates in meaningful way, give fair technical tests (which may need to be redesigned as business or market priorities change), minimise disruption to team members and, most importantly, close as soon as is plausible. Nobody likes turning down candidates - especially skilled, engaging ones - but it having to do so because the position has been filled by a great hire is a “nice” problem to have.


Inertia is critical. 

“The best people will usually have many options and the longer your process, the greater the risk they will take another role, or lose interest altogether and decide to stay put. Inertia is critical.

We recommend that, once you have clearly defined your strategy for sourcing the talent, you work to defined timescales.  Any search, however exhaustive, will only ever be a window on the available talent at that point in time.

If you are confident you have a robust strategy for getting to a strong shortlist, then you should move through your assessment, referencing and get to offer as quickly as possible.” - Sophie Eden ( Gordon & Eden)

There’s really nothing we can add to this. Fill the role. Don’t lose momentum. To be clear, we’re not suggesting rushing the hiring process, only that you must keep working as hard as you can until the job is done. That’s a big ask - nobody can work as hard as they can for a truly extended period - so aim to maximise the efficiency of your sprint.


Know your values inside-out so you can speak with confidence.

“Corporate culture is the only sustainable competitive advantage that is completely within the control of the entrepreneur.”  – David Cummings (Pardot)

There’s really no excuse for not knowing your values well before you begin looking for candidates - because without this check your shortlist is probably going to be misaligned in the first place. Once you get to interview stage, your values are what you will use to sell the business and to determine a candidate’s cultural fit. Being hesitant or unsure here is setting yourself up for failure.


If your gut says no, do a bias check - a real one. 

This need only be in your head, but your bias check should be fundamental and serious. Is it their accent? Their skin tone? Ask yourself the tough questions without guilt or self-judgement: nobody’s perfect, and we all have irrational prejudices, both major and minor. Get to the root of your biases before you ask someone else. If you’re sure that your gut feeling isn’t down to a bias of some sort, evaluate the candidate on an individual basis instead of comparing them to others to try and drill down to where your apprehension comes from.  

Do you have interview fatigue? 

Ask yourself this question periodically. If you think you aren’t operating at peak then take a proper break (making sure to keep everyone involved informed) and then get back to it with renewed energy the moment you feel able. Remember - don’t lose your momentum. 


Keep going till you close. 

When you have several promising candidates it can be tempting to take your foot off the pedal. Resist this as much as you can. Nothing is a forgone conclusion, and circumstances can upend the most seemingly locked-in hire. Maintain your energy until your new senior role is at their desk. 

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