No, I’m not fine: A leader’s guide to building a culture where it’s ok to not be ok

How to check in with employees, standardize being vulnerable, and build relationships centered on trust.

“Hi! How are you?” 

“I’m fine and you?”

“Nope. Let’s start again. How are you really? I’m really asking.”

This exchange took place between a friend of mine and her boss, and it stood out to me for many reasons. It was authentic, it showed compassion, and it highlighted a concern and awareness for mental health in the workplace in a time when many of us haven’t been face-to-face in almost a year and being “fine” is a stretch on the best of days.

It got me thinking: How can we as bosses and leaders continue to check in on our employees – like really check in on them – without prying, oversharing, being super awkward, or coming across as inauthentic? Or perhaps more simply, how do you build a team culture where your direct reports are comfortable coming to you when they are struggling, stressed, or just really not ok?  

After a bit of research and a lot of reflection, I developed a few helpful (albeit not so simple!) tips:

How to build a culture of vulnerability and trust

1 Build relationships centered on trust 

It’s one thing to know random tidbits of information about your employees like the name of their cat or how they take their coffee, and it is another thing entirely to actively build and nurture relationships with each one of your direct reports centered on trust. 

There is certainly no shortage of excellent advice on how to build trust with employees. But for me, it honestly boils down to four key ingredients:

1. Communicate often and clearly

2. Do what you say you’re going to do

3. Actively listen

4. Trust your employees from the outset

Now let’s talk about that last point for a sec because it can be a contentious one. There are definitely some managers who would tell you that an employee must work to “earn the trust” of management. If you’re in that camp I hear you – but if we’re being honest, I think that’s a bit backwards.

Saying that someone must earn your trust means you’re approaching that person with a degree of skepticism and you have decided (at least initially) not to trust them. Now think about how that might make your employee feel. You’ve decided not to trust them – why on earth would they trust you? And, why would they come to you if they were struggling?

Trusting someone is a choice you make, and sure, actions over time can indeed grow or erode trust, but a relationship of trust between a boss and an employee can have hugely positive impacts on morale, engagement, and productivity. 


Let’s look at a quick example that speaks to building a culture of trust.

The first time I found myself in charge of a team I was working with a savvy digital strategist who was very used to submitting all her social media content for review and approval. Considering this was the way things were habitually done, I agreed to review all the content but after a few short weeks I found myself strapped for time and asking – Why am I doing this? Her work was solid. It didn’t need my stamp of approval. And flexing my “I’m-the-boss-so-I-must-approve-all-of-the-things” muscles was actually wasting everyone’s time.   

Instead, I approached the strategist from a place of trust and told her:

“I don’t need to approve weekly social media content. I trust you to create content and make decisions in line with our brand. If there is a problem, a big project, or something you want to talk through, I’m here for you, but otherwise, I trust you.”

She was a wee bit floored at first, but also newly empowered. Over the next year team productivity and creativity increased, our social media followers and engagement rates grew, and overall, I found my team increasingly willing to share and talk about tough stuff – and it all began from a place of trust.

2 Leave your ego at the door (and work on listening) 

As a leader, having a big ego could indeed lead to your ultimate demise. Sounds ominous I know, but it’s true. As this HBR article points out, a big ego is the enemy of great leadership. The bigger the ego, the more at risk leaders are of insulating themselves and losing touch with their employees, company culture, and even their clients. 

And while a big ego in general will almost certainly do you more harm than good as you climb the corporate ladder, having an inflated sense of self most definitely will not make it easy for your employees to come to you in their time of need.

Think about it – No struggling employee wants to hear their boss drone on about that time they had a similar experience and came out the other side ok, or worse yet go off on some obscure unrelated name-dropping tangent. 

Let’s be clear: If an employee is coming to you because they are struggling, it’s not a time for you or your ego. You don’t need to tell a relatable story or fill the silence by trying to be profound. The large majority of the time if a direct report is coming to you because they are not ok, they really just want you to listen, understand, and leave your ego at the door.  

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3 Standardize being vulnerable and talking about feelings

For those of you who just squirmed a bit in your seats at the thought of letting emotion into the workplace, I urge you to check out the research by Brené Brown who is my go-to source on vulnerability and courageous leadership.

In her research Brené defines vulnerability as “uncertainty, risk, and emotional exposure” and notes that “vulnerability is not winning or losing – it’s having the courage to show up when you can’t control the outcome.” One quote in particular from her book Dare to Lead really underscores for me the reason it is so vital for leaders to think more seriously about normalizing conversations about feelings and being a bit more vulnerable at work.  

“Leaders must either invest a reasonable amount of time attending to fears and feelings or squander an unreasonable amount of time trying to manage ineffective and unproductive behaviour.”

You might be thinking: ok I’m all for being a bit vulnerable at work, but where do I even start and what is the line between leading with vulnerability and treading into the awkward territory of seriously oversharing and freaking people out?

Well as Brené teaches, being vulnerable and using vulnerability are not the same thing. If what you’re about to share with your team is an attempt to gain sympathy or get a particular reaction then you’re likely oversharing. But if you’re trying to lead your team through a tough change or project while admitting you don’t have all the answers and encouraging your team to share ideas and talk it through, you’re leading with vulnerability. 

4 Schedule one-on-ones (and be prepared to talk about tough stuff) 

Ok this tip doesn’t seem so difficult right? We all know that regular, one-on-one meetings are a vital part of successfully managing any team – but let me add a small note of caution here. As easy as having a one-on-one meeting may seem, going into them distracted or unprepared can have serious consequences.

An inexperienced manager may see one-on-ones as a time to talk to each employee about deadlines, review work, and assign future work – but this is actually slightly off base. 

Effective one-on-one meetings are those where the employee leads the meeting and does most of the talking. While a manager can (and should!) give feedback and discuss projects during these meetings, the meeting technically belongs to the employee. The employee should be coming prepared and ready to talk through any obstacles they are facing, get feedback, or brainstorm solutions for a particular issue. As a boss, it is your job to set those expectations and then engage, listen, and give feedback, direction, and advice. It is also your job to be prepared to talk about the tough stuff should it come up. 

Career Conversations with Employees

That’s right! One-on-one meetings are not just about assessing how that campaign performed or reviewing the feedback from that recent product launch. One-on-ones are also an opportunity for your employee to share – however directly or indirectly – how they are doing personally.

As a boss it is important to set the tone, standardize this level of sharing, and ultimately be supportive for your employees. Most importantly, when someone opens up and shares something really tough, make sure you’re prepared to respond (and not with an ego-driven response like we discussed above).

Spend some time learning how to have difficult conversations. I highly recommend the book by Douglas Stone, Bruce Patton and Shelia Heen on this very topic.

The Center for Addiction and Mental Health also has a series of free resources and webinars available for those looking to become more knowledgeable about mental illness.

It’s also a good idea to research and understand the resources available to you within your own company. And no matter what, when your employee comes to you, make sure you’re fully present, paying attention with no distractions, and actively listening. 

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5 Follow up regularly 

Now that you’ve worked through some tough tips about setting a culture of trust, leading with vulnerability, and being open and available to talk about tough stuff during one-on-ones, this last tip should be an easy one, right? Wrong. Believe it or not most bosses skip this step or forget about it completely.

Think about this from the employee’s perspective for a second – they’ve opened up to you about something challenging in their life because you’ve done a great job of following tips 1-4 and then… nothing… silence. And the employee is left thinking, What the heck? 

Leaders and bosses need to remember to follow up and they need to do so in a way that shows compassion for the employee and underscores that they have remembered previous conversations.

Instead of “How was your weekend?” try questions like, “Did you end up going on that hike you were talking about?” or “Were you able to take some time to look up those resources I mentioned?”

It’s also a good idea to keep some notes from one-on-one meetings and refer back to them before the next one-on-one with that employee. Doing so will signal to the employee that you have indeed remembered previous discussions and you care about them, their success and their well-being. 

Pro tip: using a one-on-one meeting tool like Fellow can help you keep track of all your meeting notes, reminders, and takeaways in one place.

One on One Meeting Tool

Remember, as a leader and a boss, it’s ok for you to not be ok too. And it’s not your job to take on or solve all the problems for your employees. But it is your job to create a culture and an environment where your team can thrive – even in a time when everything might not be “fine.”

Don’t lose sight of the fact that improving the culture of a workplace or team does take time – a lot of time. Go slow, build incrementally, celebrate your wins – just don’t forget that the most important step is to start.


About the author

Samantha Rae Ayoub, MA, CMP is a consultant and advisor who helps her clients meet their business objectives through people-centered communication and operational strategies.

She has led high-functioning teams in the non-profit, hospitality, and volunteer sectors, and throughout her career she has worked with numerous CEOs, COOs, Executive Directors, scientists and researchers.

Samantha has a Masters degree in Professional Communication and is an internationally certified Communication Management Professional. She is a former President of the Ottawa Chapter of the International Association of Business Communicators and remains an avid volunteer and leader in the community. 


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