I’m listening to a familiar story.  It’s from a former co-worker of mine who began a job at a start-up six months ago. He’s now quitting. While he told them during the hiring process that he would need a flexible schedule and potentially time off due to a parent’s health, they are now unable to accommodate him upon that parent’s passing. Why were they okay with hiring him during the interview process, and now not comfortable with the reality of what he needed? That said, my friend wasn’t surprised. Since being hired, he’d noticed the high octane workstyle of the C-suite and the high expectations of others that went along with that pace. 

Why was the startup so willing to hire someone who said he needed flexibility when they couldn’t act on it?

Why have I heard about this kind of situation multiple times with start-ups? 

While I was annoyed on behalf of my friend, this situation is very common and is a rising topic of interest even in the manic world of start-ups. Amazing work can result from a busy pace, but so can burnout and other side effects, like lack of diversity in the workforce. With the rising interest in flexible working and increasing studies and surveys into its benefits, why do we still have such hardline views in the startup space?

Kristine Coco is a startup expert. She’s worked in leadership roles at Fitbit, Fitstar and ngmoco and she now owns her own consulting company focused on helping growing startups unlock organizational efficiency while scaling. I turned to her to help me explain what I’m seeing and why. 

Kristine notes that startups measure time in days and hours, not weeks and months. With a finite runway and window of opportunity, it’s important to move as fast as possible, and sometimes this conflicts with employee flexibility and even the company’s perception of their own culture they are hoping to achieve. 

“Flexibility” is a broad term and means a lot of things to a lot of people. It can mean the flexibility to work from home, work a reduced schedule, come in late, or, as in the example above, a need to take some time off to care for a family member or themselves. 

Flexibility also has a different meaning than the often-used phrase “work life balance”, which refers to a more holistic approach to well-being where a satisfying work life and personal life can be achieved. However, a good approach to flexibility can help with work life balance by helping your employees achieve life goals.

In her experience, some of the most common situations that interfere with systemically providing employees with the flexibility they require:

  • High priority meetings getting changed last minute
  • Meeting culture and communication practices are geared toward being in-person 
  • Plans and schedules that constantly evolve, making it difficult to predict when is a good time vs a bad time to be absent 
  • Decisions that must be made quickly and require input from employee with expertise or knowledge no one else has

It’s worth noting that the above can also contribute to burnout, so flexibility is worth thinking about as one approach to helping with your employees’ long term motivations and endurance.

Taking Charge

The good news is that those challenges can be overcome with proactive and thoughtful leadership. With our collective 40 years of experience in the tech space, here’s our advice to startup CEOs (and employees): 

1) Define how important flexibility is to your culture

Start-ups often have a “we’ll sleep when we’re dead” culture with 24/7 schedules for a very practical reason: investment dollars run out and every minute does matter. 

That said, more and more employees are expecting a flexible work environment, and it will behoove you to think through what this means for your company.  There is often a knee-jerk reaction that equates flexibility as detrimental to the business and the culture, but that isn’t always the case. It’s worth digging into specifics on day-to-day work.  Are employees evaluated on their deliverables versus their availability? Are milestones at risk? Do co-workers need to take unreasonable steps to compensate for another co-worker’s flexibility? 

Think through what flexibility looks like for both your employees and the company. And then dig into how and if you can you integrate that into your values and culture.

2) Define “flexible”

When your company says you can be flexible, what does this mean? Do you mean a day off here or there? Do you mean on-going work from home? Be specific. Remember that the more flexible you can be, the more types of people it may bring to your organization: working parents, single parents, adults with aging parents, adults with chronic or acute medical conditions. These additional people you’re able to support could bring interesting and vital experience to your company. 

Don’t forget that flexible could also mean allowing space for someone who’s taking care of their own well-being, who knows what they need to stay healthy, whether through regular exercise, doctor’s appointments, or classes.

For prospective employee, be specific about what you need. Make sure the hiring manager is really understanding what you want and need. If you need every Thursday afternoon off for swim lessons with your child, be specific so there are no surprises down the road.

3)  Engage during interviews

If a prospective employee says they need flexibility, engage in that conversation. Ask questions and think about whether you can accommodate this or need to negotiate. Most employees will not bring this up if they don’t really care or need it. Why would they put a kink in the hiring process unnecessarily? Therefore, if they do bring it up to you, it’s because they truly need the flexibility to make their life work. Don’t benignly accept whatever they say to close the hire. 

Getting hired? Be wary if they say yes too quickly without questions. And don’t simply accept the recruiter’s assurances. Also talk to the hiring manager and other team members about their experiences. Make sure this is right culture for you!

4) If you believe in it, model it

I once had a manager who took two days of his more generous parental leave off. He certainly did not object to other people’s parental leaves, but he modeled the opposite behavior. And of course actions speak louder than words!

Kristine used to leave work at 3:30pm on Tuesdays for a standing appointment. She was offline until dinner time and would regularly go back online in the evening to finish her work. She would send a flurry of emails and Slack messages, and she quickly learned to clarify that she didn’t need an immediate response from coworkers whose schedule didn’t include a Slack conversation while making dinner. Or, in the case where they had an urgent request, she would check on what time was good to work together to resolve.

If you say you believe in flexibility, then it’s really the day-in and day-out behaviors that will prove it. How do you react when people need time off? Do you pepper them with urgent requests or enthusiastically work with them to figure out how to support their request?  Are you constantly emailing during your vacation and holidays? People will take note and react to that as the true culture. 

5)  Invest in HR early

Supporting flexibility is possible, but it requires explicit conversations about what will and will not work and why, investment in systemic solutions such as video conferencing and real time collaboration tools, and a willingness to change the status quo. 

One of Kristine’s prior startups supported remote work. To support this, she asked all employees to use the Working Hours feature on their Google calendars so they wouldn’t accidentally be booked for meetings when they couldn’t make it. They also invested in making sure video conferencing was super easy to use for everyone from anywhere. Google Hangouts + Chromebox is a great solution here, as is Zoom. 

Does the 5pm weekly meeting really need to be at 5pm? What software can be used in lieu of a physical whiteboard to support remote team members participation in a problem solving session? Are employees being evaluated based on their results or is ‘facetime’ a criteria?

What if you just can’t?

As you explore the above, you may find you’re not actually supportive of flexibility. That’s ok! Own it, and be upfront about your culture to your team members and prospective employees. 

  • Look for employees as passionately available as you are for the early days. 
  • Be upfront with your prospective hires about your expectations, and understand those choices may have an impact on diversity and the culture you are setting.
  • Know that you may sacrifice experience and sometimes even quality here, as seasoned employees tend to expect balance, and a burned out staff can make mistakes.

As long as everyone is aligned with expectations, your startup can be on its way to success with the talent and workflow model that best works for you and your staff. Remember to stay open to a more sustainable model and culture as your company grows. 

As many successful startup CEOs can attest, the “always available” model isn’t sustainable in the long term and may, in fact, impede your progress overall. Set a more balanced tone for your life, team, and company and your success will most likely follow suit.