Type your search and hit enter
Why you should interview your next boss

Why you should interview your next boss

Knowing about this person’s background and own career motivations is critical

As a CIO we all have different experiences with our supervisor. Of course there are huge variances in who we report to – the CEO, COO, CFO, global CIO or regional CIO for example. In each instance (and I’ve had experiences with each example), there are pluses and minuses.

When you are the CIO and report directly to the CEO, then there should be no issue in understanding your accountability and sense of responsibility. You are ‘on the hook’ for everything. In my opinion, any role that allows for that level of clarity is ideal.

Now back to this notion of interviewing your next boss. When you are going through career transitions there are many factors in your mind around job satisfaction, salary, level, work challenge, stress and the list goes on. In the interview process you are assessing and weighing up these factors and in your own mind making an overall assessment of the desirability of the role.

The most important factor however is to interview your next boss and make a judgment how well you believe you will work together.

The interview

First, knowing about this person’s background and own career motivations is critical. Whether the boss is male or female, younger of older – should make little difference in the end. You have to assess the emotional intelligence as well as what you can ascertain on their intellectual capacity.

There is always a good saying that learning from your new boss is a motivation. That’s very true and we all learn positive traits from great leaders. I believe you can make a reasonable judgment of the person’s intelligence, what your can’t judge as easily is the behaviour under pressure.

I recall once meeting a global CIO who was known as a straight shooter, very smart and ambitious. As I probed and asked questions around the capability gaps in the enterprise; what I received was a resounding ‘no’.

“We are world class,” the CIO said.

However during the discussions in the next few minutes, there was awkward admission that actually there are gaps. Immediately, I recognised that this global CIO had incredible pride and while this is a great strength, it can also be a weakness. I knew at once that I could not work for this executive.

What I look for

In many ways you seek a boss that has similarities to yourself. But you also have to value the differences. When you work for a boss that you can anticipate how they think – that’s ideal. It just doesn’t mean that you should therefore do everything to please him or her. Instead this allows you to anticipate and work with your boss, proactively.

I’ve worked in large enterprises where I’ve witnessed executives who take the role modeling too far, to the point of imitating the verbal expressions, dress code and other traits. While this is not hero worship there are dangers in following blindly. My key point is that a good CIO has to know when to disagree and push back on his boss.

This thus is a great question for you to answer in the interview. 'How would this boss take it when I disagree with him or her?' If your answer is that it wouldn’t go well, then I suggest this would be a difficult place to be an empowered leader.


A great trait that I value is continual learning and being able to myself practice learning agility. For a CIO, this is an essential trait and will afford you the opportunity to try to stay up to day with rapid developments and change.

What I don’t mean is having the boss commit to send you to a development course. These can be great but by learning I mean a more ongoing commitment.

When you meet a boss who talks about – how they learn and devote time to this; either individually or as a team, then you have a great sign. Every great boss that worked with was committed to this and allowed their leaders to ‘sharpen the sword’ as Peter Senge wrote.


Not every leader can be strategic or indeed the smartest person in the room. What is valued to me is a leader who takes the input from his executives including the CIO and applies perspective in making business decisions.

For me perspective is being able to look broadly and see how to ‘join the dots’. Having an ability to think in terms of time horizons 1, 2 and 3 is what I would look for. Once this is broad vision is painted then I also look for evidence that there is discipline for the execution. If you are able to see such traits then you have come across a boss who could be very inspiring.

Change agent

The best bosses that I have worked for have been change agents themselves. They are simply motivated by making change happen. It doesn’t need to be labeled as transformation or digitalisation or re-engineering.

The great boss just wants to drive this change and have a CIO as a partner to work with him or her. For any CIO, if you are not in the environment that is wanting to change and make radical improvements then your industry is going to be disrupted.

Yes, I have a bias for change and transformation. Most CEOs have the exact same drive and the only question around the appetite for change is the pace of this transition.

Honesty and integrity

Finally, I look for this in my boss. I can put up with egos and even some bureaucracy. The CIO wants to work for a boss that has strong integrity and honesty. Without these traits it is hard to feel passionate and committed to the boss.

Ok, the interview is over. The question is, ‘did I get the job and do I want to work for this new boss?’

Join the CIO Australia group on LinkedIn. The group is open to CIOs, IT Directors, COOs, CTOs and senior IT managers.

Join the newsletter!


Sign up to gain exclusive access to email subscriptions, event invitations, competitions, giveaways, and much more.

Membership is free, and your security and privacy remain protected. View our privacy policy before signing up.

Error: Please check your email address.

Tags David GeeMetLife

More about indeed

Show Comments