A Question That Every Manager Should Ask

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I remember like it was yesterday.


In a small park in northern San Francisco, my boss and I walked around a park for our one on one meeting. As our first one on one meeting, I had no idea what to expect. The conversation started as a typically meeting would. What his expectations were, how he liked the team to run, meeting teams, etc. However, half way through the conversation, he dropped a bomb.


Manager to Direct Report ~ “Where do you want to go in your life?”


How am I supposed to answer this question? Is it a behavioral one, or is he trying to catch me in a trap? At the time he asked me the question, I lied about what I wanted to do because I thought the answer was what he wanted to hear. The lie- rise up in the company. It took years for me to understand what this question really meant. In addition, why every manager should ask each person on their team this question.


Companies today experience the highest levels of turnover in the past 10 years. Regardless of what industry you are in, you are affected in some way. Whether that is from a financial, team dynamic, knowledge transfer, or deliverables, losing someone has immense impact on the organization.


The question, ‘Where do you want to go in your life’ is paramount to understanding the fundamentals of employee engagement. If the employee is not aligned with their position, then they are more likely to leave. Looking at this point deeper, when someone is not on a path that entices them, they are more likely to sack off, cause a lack of fulfillment, leading to turnover. Unfortunately, many company positions are made not with the employee in mind so ‘a square peg round hole’ is common.


So what do employees do as a consequence if they don’t leave? Well, according to Recruiter.com 85% of employee have some sort of side hustle. As probably anticipated, there has been a lot of tension between employer and employee about picking up a side gig. In an article posted on Recruiter.com it read:


“Our data simply reinforces the need for greater dialogue between companies and their workers to set boundaries that allow for side gig participation in a responsible and productive manner,” says Billing. “As the race for talent escalates … employers already are walking a thin line with regard to retention. Should they set stricter policies or attempt to limit workers’ involvement in side gigs, those workers may opt to seek roles at other companies [that are] more accommodating of their interests.” Recruiter.com


Hence, side gigs are becoming now a value proposition that certain employers are usually to attract candidates. Now back to the question.

So What Does This Question Really Mean?

The answer uncovers the main motive for an employee to join a company outside. They may want to travel the world, become a musician, or maybe they just want to become the CEO. If a manager can uncover this, they have essentially acquired one of the best keys for motivation.


In order for this question to work effectively, there are three parts to be weary of.


The first part focuses on the relationship openness between manager and direct, as known as  trust. Internal company surveys find that 80% of managers said they’re transparent with their teams while just 55% of employees agreed. Hence, teams can lack trust and managers struggle to spot it. In order for an employee to open up with their manager about what they truly want to do with their careers outside of the job they need to have trust as a pillar.


If you do uncover what someone wants to do with their career, the second part is how do you go about empowering them without it undermining the position? At this step, it comes down to monitoring expectations and setting clear guidelines. Often, managers struggle with this step because the expectations usually consist of showing up for 8 hours everyday and do the best that you can. Unfortunately, that is far too vague and there needs significant detailing to avoid confusion. For instance, how many projects should be completed everyday, measuring against KPIs, etc. Once the guidelines are in place, an employee can pursue their dreams while also acting in the confines of the company.


The third part revolves around a mindset dilemma. An employer, or manager, could feel that if their employee is able to work outside of the company, they could have more energy to spend at their job. There are two schools of thought on what to do in this case. One side, if an employee has a salary job, they should be fully commitment to that job. On the other hand, an employee should commit to their job within their given working hours and expectations. My stance on this issue is that if someone wants to earn income outside of their job, then they will inevitably do that no matter how much you control them. Hence, its best to embrace the balance of side and main gig but let your expectations be known.

Companies Becoming Advocates

Many companies have recognize this dilemma and as a result institutionalized ways that they can harness this desire by adding internal incubators. In some of these internal incubators, if an employee has an idea, companies would provide the necessary resources in exchange for part of the company. This way, instead of an employee leaving a company to fulfill ‘what they what to do in life’ the corporate entities can financially benefit in the long run and the employee gets to do what they want. Win-win.


While this may seem too naive of companies, let me remind you that companies like WhatsApp were created by ex-Facebook employees and Facebook later acquired WhatsApp for $19.6 billion. What if Facebook opened up internal incubators at that time and the WhatsApp founders stayed at Facebook?

What to Expect in the Future

While this simple question of asking your direct report about their career direction may seem simple and unnecessary, we inch into a new workplace – The Gig Economy. In this economy according to TechTarge ‘A gig economy is a free market system in which temporary positions are common and organizations contract with independent workers for short-term engagements.’ Making it more and more common for employees to have several projects spinning at the same time. The gig economy continues to fraction out various industries: house cleaning, mechanics, driving, grocery shopping. Employers, as a result should expect full time employees now have the ability to become part time contractors.


Will you confirm to this trend? Or will you push back against what your employee really wants to do with their career? It’s a difficult question because it could affect your bottom line either way. Change is upon us whether we like it or not. So I ask you ‘where do you want to go as a manager’?


Jeff Butler

Jeff Butler Internationally respected speaker and consultant, Jeff Butler helps bridge generational gaps between Millennials and companies looking for their talent and patronage. Butler has quickly built his reputation as a memorable presenter with tangible solutions for attracting, retaining, and engaging Millennials as employees and customers. Within just the past three years, he has spoken at two TEDx events and multiple Fortune 500 companies such as Google, Amazon, and LinkedIn.


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