3 Career Questions to ask your boss . . . NOW!

Has your career lived up to your expectations? If not, It’s not too late to make a change. You just need to be asking the right questions.

jon-hansen questions

Last year Kelly Barner and I spoke at a public sector conference regarding the key findings from our book ‘Procurement At A Crossroads: Career-Impacting Insights Into A Rapidly Changing Industry‘.

In the two sessions we gave, we posed the following two questions to the audience.

With the first we asked, how many of you chose procurement as a profession?

For those of you who have been in the industry for some time, you will appreciate the thought process behind our query, as historically very few people actually chose purchasing as a career. Most sort of fell into the role.

Based on the response, it is clear that times have obviously changed. The majority of people raised their hands indicating that procurement was indeed, their profession of choice.

If You Could Turn Back Time?

We then asked the second question. Knowing what you know now, and if you could do it all over again, how many would still select procurement as a career?

In both sessions, regardless of age or length of time on the job, the response was the same. Approximately 50 per cent of those in the audience indicated that if they could go back in time, they would have made a different career choice.

The reasons they gave were varied, and are in and of themselves, worthy of a separate article. However, and corresponding with the focus of this post, there was a central or common theme. During the hiring process it appeared that very few asked their prospective bosses the right questions.

In short, they were more focused on being hired, without really understanding what the actual position entailed beyond a perfunctory role and responsibility job description. This I believe, is a common scenario that is played out across all professions in all industries.

Based on the above responses, it is imperative that job candidates ask the right questions.

So what are the right questions?

As a procurement professional, these are the three I would ask:

  1. What is your view of technology, especially in relation to its role in the procurement process?
  2. What is your approach or process for engaging key stakeholders, both within and external to the enterprise?
  3. What, if any, changes will we see in procurement in the next 2 to 5 years, from both an individual professional standpoint, as well as collectively?

By the way, it is never too late to ask the above questions, even if you are already nestled into a procurement career. The responses you receive could surprise you and, perhaps, give you a renewed enthusiasm for your chosen profession.

Now you may be asking yourself, why these three questions?

Because the answers you receive will reveal the true attitudes and values of your boss and the organisation as a whole.

The Technology Question

For example, take the technology question.


If your prospective boss (and company) are heavily invested in making technology the primary focus of their efforts, then you will be in trouble.

While technology can obviously play an important role in automating the procurement process, thus freeing up valuable time for you to focus on more strategic endeavours within the enterprise, in and of itself, it will not get the job done.

As a supporting resource, technology requires people with an ability and desire to openly collaborate with key stakeholders which, not surprisingly, serves as a lead-in to the second question.

So if your prospective boss places a great deal of emphasis on technology as being critical to procurement’s success, that is a red flag. It means that you will likely find yourself relegated to a supporting role, as opposed to having a leading role, in the organisation’s procurement strategy.

Engaging Stakeholders

In terms of the remaining two questions, let’s start with the approach and process for engaging stakeholders.

For far too long our profession has operated in what I will call the zero sum game vacuum. Specifically, the belief that in order to win, someone else has to lose.

For example, during a lecture Kate Vitasek gave a couple of years ago, she talked about her time in purchasing with Microsoft. The co-author of ‘Getting To We’, who now champions the principles of being relational, recounted how she would be rewarded financially for driving down a supplier’s cost, even if doing so had negative consequences for said supplier.

IACCM’s CEO Tim Cummins also talked about how senior executive stakeholders at the negotiating table would routinely lie to one another about what they could do, by when they could do it, and for how much.

So when you sit across the table from your prospective boss, you need to determine if win-win is a vague sentiment without any real substance, or if they really understand the new dynamics associated with building relationships based on collaboration and transparency.

Change and the Future

Finally, let’s talk about question 3.

Asking your prospective boss to provide you with their take on how the industry and profession will change, may seem like a catch-all, pie in the sky question that is more likely to produce a perfunctory response, as opposed to eliciting meaningful insight.

However, if the answer you receive stands out from the same old generalisations one usually hears, you will know it. This is because it will reflect an attitude of new possibilities. An attitude no longer held captive to the traditional views of what our profession and industry is about.

In essence, this last question walks the talk of the first two. The answer you receive will legitimise the response for the first two questions. Because without change – or an understanding of what needs to change – improved stakeholder engagement and the proper assignment of technology is not possible.

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