When it’s time for a career move, many high-calibre candidates often have a number of job offers and will ask our advice on which to take. Sometimes the opportunity to prove yourself by sorting out ‘a mess’ is a sure way of adding some sparkle to your CV. But how do you distinguish between the role that will shoot you to even greater glory and the one which turns out to be a career killer?

It’s the conundrum of the poisoned chalice or dream ticket and after speaking with hundreds of candidates about this topic and finding out about their progress further down the line, the reality is that for some jobs the challenge may simply be too big.

We are likely facing a unique moment in time where the immense scale of the digital giants such as Amazon, Google, Apple et al, combined with a convergence of technologies that are rapidly maturing (AI, 5G, IoT etc.) and an enormous amount of private funding available to invest in promising emerging businesses will challenge industry incumbents like never before.

Given the pace of change and the opportunity to measurably move the dial, many candidates are looking to be involved in businesses experiencing transformation or in need of turnaround. If that includes you, a critical step is to identify which organisations are likely to have an environment where executing transformation is probable versus those that might make the right noises but will ultimately get bogged down in legacy culture, legacy systems or a complacent management team that will render successful transformation unlikely or impossible.

In this piece, myself and two other senior partners discuss how you can tell the difference between the poisoned chalice and the dream ticket. Between us, we have more than fifty years’ experience in recruiting senior executives for some of the worlds’ biggest and most prestigious businesses and have helped many executives follow the path to a dream ticket role.

1. Assess the Quality of the Leadership

In our experience, the businesses that have strong leadership (particularly in the CEO seat) are the ones that tend to deliver on their ambitions of change or turnaround. If you are interviewing with the CEO consider asking:

  • “What are the challenges you face?” Note the way they organise their response – is it logical, cohesive and compelling?
  • “If you could wave a magic wand, where would you be in 6/12 months?” This gives you an indication of the realism behind their ambition and cuts through the logic to start to understand their emotions
  • “What are you like on a good day and a bad day?” A question to check their self-awareness. This can then be cross checked with other Exec team members you meet.
  • “What do you find as the toughest part of your job?” Are they self-deprecating? Do they acknowledge where they need help?

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2. Check Alignment Across The Executive Team

It’s important to meet a variety of key stakeholders within your interview process. Check:

  • Have they offered you the opportunity to meet the Exco or a just a handful of middle managers?
  • Have they given you a clear timetable and budget as transformation might be never-ending?
  • Have they explained the boundaries of your role and how to get stuff done outside them?
  • How are they going to measure your performance in year one and two?

Alignment is crucial in delivering transformation, and mixed messages or differing ambitions are a warning sign that the internal challenges within an organisation may be too great to drive successful change.

Similarly, having spoken to a number of people across the interview process, check that they are all saying the same thing. Does the brief from the search or interim firm match what the business is telling you when you interview?

If you don’t get the same, clear answers from all key stakeholders – step away from the role.

3. What’s the Context of the Organisation?

Business has decided they want or need to transform, but how committed are they to do what needs to be done?

  • If they are a PE backed business, then the likelihood is there will be a real pressure to deliver and get things done
  • If it’s a FTSE100 or 250 there will be pressure from the board, however unanimous, agreement about how extreme the change needs to be can differ so look to sound that out
  • If they are a public sector business it can be more difficult to assess. Many public sector businesses will have grand schemes but can often struggle to deliver because of lack of money and bureaucracy.

With your due diligence, also take a look at the governance structure. If it feels like a labyrinth in its complexity, then that should also be a warning sign.

4. Culture Compatibility

When doing your due diligence to understand whether you’re likely to thrive or not in the role on offer, consider the culture of that organisation and be brutally honest with yourself about whether your own values and behaviors are aligned. Even if the role is a dream ticket, if the culture isn’t a fit for you, it could be a hiding to nothing.

Finding out about the culture is less about reading what’s stated on the website, or what you may have been told, but can be gathered by conversations you have with trusted advisors, previous employees that you may have a connection with and by asking the right insightful questions throughout the interview process. A dream job in the wrong culture for you may end up being short-lived. It could be the difference between career progression and a painful experience.

Even if the role is a dream ticket, if the culture isn’t a fit for you, it could be a hiding to nothing.

5. Gut Feeling

When looking at a new role, either internally or externally, if you’re able to answer the other questions with a positive response then it’s likely that the answer to this question will also be positive.

If you have any reservations about culture compatibility or your questions are not getting answered, then your gut will tell you that it’s not the right move and you should reject the role.

In addition to this, there are the roles which may fit your personal brief but are just too easy. Everything that needs to be done has been done and even if the salary is appealing, there will be no opportunity for the transformation or change programme that really showcases your talents.

Final Thoughts

The real trick is for a senior leader to get as close to the line where the dream ticket dissolves into the poisoned chalice, but just before it does. When there are massive problems such as weak relationships within the business, low morale, underperformance and major programmes to be rescued – these can be fixed, by a person of talent, integrity and tenacity, in other words, you.

It’s a fine line and often the real moment of truth will only come three to six months into a new role, but by being cautious and extensive in your due diligence ahead of accepting the role, it will help you identify any of the warning signs that this job may not be for you.

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