Thriving in Tech – A conversation about tech company culture, work-life balance, & breaking into tech cultures

Thriving in Tech – A conversation about tech company culture, work-life balance, & breaking into tech cultures

JobStep’s CEO, Eleanor Meegoda, sat down with Jillian Hufnagel, JobStep Advisor and Head of Culture at Slim.AI. They talked about thriving in tech company cultures. 

Below are some tips and highlights from the webinar

How did you break into tech?

[I’m an] “art school dropout turned receptionist, office manager, executive assistant, Chief of Staff, head of culture, coach, and advisor. My career has not been linear. Most people’s careers are not linear. I love working with startups.

I’m a Mom of two. I have a 10th grader who’s 16 and an almost eight-year-old who’s in second grade. Homeschooling is no fun for anyone at my house. My kids are finally back in school, which is awesome. 

I attended Mass College of Art for a few years, and my plans changed when I had my first baby at 23 and had to work full time. I transitioned into working in a hospital and doing appointment scheduling. I realized that I hated being in my chair at a certain time, else I was in trouble.

During high school, college, and after, I did a lot of waitressing and bartending, starting at age 14. For any of you familiar with Inman Square in Cambridge, the East Coast Grill is where I learned to love food.

There was a restaurant that I worked at after college with a mill building across the street that had a ton of tech companies in it. I never thought I would get into tech; it wasn’t intentional. I had restaurant customers coming in who I got to know who worked for a video game startup. 

They were super awesome people – artists, designers, and engineers – many of whom are still dear friends today. I formed relationships with them, and the impression I made was a good one. I was myself – curious, approachable, and willing to meet my customers’ needs. I got offered a job to be their reception/office manager/admin at that tiny video game startup with about 30 people, where I got to wear a lot of hats.

The important takeaway from how I broke into tech is that when you can be your authentic self, people see that and they’ll know whether or not it will fit in their culture. 

Now, I’m on my 9th startup.


How do you know if you’ll have to wear a lot of hats at a tech company?

“Part of it depends on the scale of the organization. Some startups will be further along than others. 

One of the things you want to understand is ‘how big is the company? How far along are they?’ If they’ve got more than 50 employees, you’re not going to have to wear a lot of hats. If they have less than 20 employees, you’re probably going to have to wear at least a couple. 

When you get in ground level at a really small startup, you get to  dip your toe in over here in accounting, and you get to dip your toe over there in event marketing, then you find yourself supporting fundraising.“


How do you figure out if a tech company is for you?

For people who like building processes & wearing many hats:

“What’s really fun about startups is that they are kind of like Silly Putty. They’re soft, squishy, and moldable. When you try to put them into too tight of a construct, they tend to not stay in that shape. If you’re the type of person who thrives in structure, I don’t think you want to look at a startup unless it’s very well established.” 


For people who like structure:

“If you like structure, you’re going to want to look for later-stage startup organizations that are “series C” or  “series D”, meaning that they’ve raised multiple rounds of funding, and they’re probably either looking at an IPO or looking at being acquired. What happens in that phase of the business is they have to get all their ducks in a row. They need to have everything documented, have all their file structures clean, and start acting like a publicly-traded company. They can’t be messy or loosey-goosey anymore.” 


All companies are becoming a little bit more volatile. So a technology company might be as safe or a better bet than a large, old company, depending on the industry. 

“Some of the companies that I’ve worked for have been acquired, and I have rolled into very large global organizations. And to me, it feels like having my candle put out; it’s just not for me. What is true in organizations that grow through mergers and acquisitions is that they likely also have structured layoffs regularly. 

Large organizations that are publicly-traded to hit their margins and make sure that they’re doing what’s right for their shareholders need to grow and shrink with the market. You might assume that going to work for a large global company is going to give you more stability than a small startup, when in reality, they probably have two to three structured layoffs every year.”


What should you do if you’re not great at assessments, but you get one in a recruiting process?

Remember that it’s just one part of the process.

“Think about testing as just one piece of the component. Testing can be on technical skills, soft skills, or testing to see how you react when you’re uncomfortable. 

Because it’s only one component of the interview process, a test result is not necessarily an open and shut case; it’s just one more thing that employers look at when they’re trying to consider the holistic approach. 

If you know you’re bad at taking tests, you should tell them that tests give you anxiety. You should tell them that because that’s your authentic self. You don’t want to be the square peg in the round hole or the round peg in the square hole. 

You want to thrive. If you can’t be your authentic self, because maybe testing is part of that job regularly, and it’s going to stress you the heck out. You don’t want that job.”


Ask them what an employer is trying to understand about you with this assessment.

“You can say, ‘I’d like to understand what do you look for in the output of these assessments? What are you actually looking for? Are you trying to understand how quickly I can accomplish a task? Are you trying to understand whether or not I will get nervous? Are you trying to understand whether I have a hard skill.’”


What are some questions to ask to suss out bad culture?

Ask questions to assess how your manager and the team address conflict

“I think one of the things that we do as humans is we associate good and bad. When in reality, everybody’s messy. I.e., companies are messy! They are full of messy people. You want to suss out: ‘When there is a conflict, how is it addressed?’ “

You can ask: “If I were your employee, and I had a conflict with one of my peers, how would you address it? 

Potential Red Flags: If the hiring manager says: “Oh, I would go talk to that person’s manager, you’re gonna probably want to be like, why aren’t you teaching me how to have healthy conflict?”


Ask questions to see whether the company and hiring manager run things in a way that matches with how you thrive. 


“This is really important. 

Tip: Think about a teacher, a mentor, a parent, a family member, someone in your life who you look up to, who was there for you, and who helped create an environment for you to thrive. 

Were they the type of person who was sitting next to you saying, ‘Let me show you how to do this, I’m gonna teach you how to do it, and then I’m gonna let you try.’ 

Or were they the type of person who said, ‘I’ll push you off the cliff, and you just raise your hand. If you need the flotation device, I’ll throw it to you.’ 

We all thrive differently. 

You want to suss out whether or not the hiring manager, the team, and the organization create the environment that YOU can thrive in. Some people actually like to be pushed off a cliff and say, ‘I got it. I’m going to try this on my own; I’ll let you know if I need help.’ You want to think about culture directly related to how you thrive.” 


Reflect on what your non-negotiables are and ask questions to see if the company will make space for that: 

“Think about culture directly related to what are your non-negotiables.


For example, do you have a family that you’re supporting? Do you have someone that you’re taking care of? An organization that expects you to work 70 hours a week is likely not one you can thrive in. Cliffnote: those people working 70 hours a week always burn out.”


Remember that you should assess the company as much as they assess you.


How do I show up and succeed in a tech job in the first 30 days, 60 days, and 90 days?


Tip: Have ownership of your professional development. 

“As the head of culture, I support that by engaging with my employees to say, ‘Is there a methodology or a tool or a skill set skillset that you don’t possess today that you’re curious about that you think would benefit you?’ I’m not doing that unless the team member is coming to me saying, ‘Can we have a professional development chat?’ It is key that they are also talking to their manager regularly in 1:1s about their growth. You have to take ownership of your development: what you want to learn and how you want to grow.“


Tip: Ask lots of questions: 

“Another thing that’s important to your career development is especially when you’re in tech, or you’re transitioning into tech. You need to ask questions.” 


Tip: Take time to learn how things are currently being done.

“You’re going to bring skills and competencies to the table that will come to bear that will benefit the team. That can’t happen if you’re not learning what already exists. You need to take time to actually read the handbook. There’s context in there that’s important. Take time to get to know people on your team.”


Tip: Take time to actually get to know your new colleagues as people

“Actually get to know people, book a coffee with them, if it’s over zoom, fine… It’s important to spend time learning who the other humans are that you’re sharing space with, even if it’s virtual space, because what ends up happening is you create common understanding, and you create mutual caring and mutual respect. 


When you create common understanding, caring, and mutual respect – then people are excited to hear your ideas. Nobody will listen to you if you don’t take the time to get to know people to try the process as it exists. Then you can influence for the better.”


Tip: Replace “sorry” with gratitude

“When you ask questions – follow with gratitude, not an apology. Don’t say: “Sorry to ask but…” Instead say: “I have a question. I really appreciate you taking the time to answer it.”


Say: ‘Thank you for taking the time to show me.’ Don’t Say: “I’m sorry, I can’t find it.” No one wants a mousy apology. 


Never start a question with “this may sound dumb”!


You’re asking questions so that you can be more resourceful and effective in your job and make the whole business run better.“


Tip: Imposter Syndrome is real. But you are not an imposter. Give yourself grace and time to learn. And don’t let the feeling drive your behavior.


“Imposter syndrome is real. It’s going to happen. It doesn’t matter if you’re changing verticals or if you’re going from non-tech into tech. Every time you start a new company, you may think, ‘I hope they don’t actually see that I can’t do this’ or ’I hope that they don’t think I’m incompetent’ worse ‘I don’t feel like I belong here.’ Imposter syndrome is real. You need to give yourself grace and not let it drive your behavior.


One phrase you can use with your colleagues: “Thank you for showing me this. I know you already showed me and I forgot. Please show me again, and I won’t forget.”


Tip: Startups are moving at a pace of a tornado. Be proactive about finding answers or figuring out the answers on your own. 

“Another analogy I want you to think about is, especially in tech startups, the organization moves kind of like a tornado. There’s not a lot of rhyme or reason in very early-stage companies. It’s literally just everybody getting together to try and figure it out. FITFO: “Figure it the fuck out.”


You’re walking into a tornado, and all these people are spinning around you. You need to be able to pull things out of the tornado to find your footing. Sometimes that’s asking for help, sometimes researching, or even asking if you can sit in a cross-functional meeting to learn how another team or another department does something. You’re a student, and you need to observe to learn.”


What do you look for in new hires and new team members?

“When I’m thinking about hiring someone into a startup, 

  • I look for curiosity, self-reflection, and aptitude. 


And part of the aptitude bucket is that you know enough to ask for the training you believe you need. You’re self-reflective enough to say, ‘I’m over my skis,’ ‘I don’t actually know this.’ Consider if you need to go learn, find a tool, take time to research…Ask yourself, ‘do I need to go listen in on some other experts talking about these things?’ 


Your baseline skills and competencies that you have today are going to keep evolving. Beyond that, what soft skills/hard skills should you grow – because maybe you suck at them. That’s your self-reflection: knowing where you are not strong & focussing growth there.


When you’re self-reflective, you can ask questions like, ‘Am I the thing that’s holding the project, the program back? Is my ego holding us back? Am I being stubborn – “Because I know how to do it,” and I’m not listening to the team. Maybe ‘I haven’t called out that we have a budget gap. 


Maybe I’m afraid of going to my manager to tell them that everyone on the team thinks this is a bad idea and no one will say it.’ That happens in startups.”


About Ageism. Should I still apply even if I’m a mature professional?


Tip: Consider tech & startups if you thrive in change

“If you do not thrive in change or are not willing to try to thrive thru change, I would have you pause on whether or not you want to go into a startup, especially in technology.”


Tip: If you’re nervous about tech, see that as a growth opportunity & go after it!

“If you’re scared to do it, that means it’s a growth opportunity for you. If you can get to go into your growth zone, you will be a better version of yourself & challenge yourself. If you’re saying to yourself, ‘I’m too old for this’ or ‘I can’t learn new tricks,’ you’re limiting yourself by having those thoughts and those beliefs. The reality is, you bring a lot to the table.”


Tip: Own what you bring to the table

“Diversity, Equity, & Inclusion are increasingly important in tech, and diversity includes age. 


I love spending time with people who are just about to retire because they look at the world differently than I do, and I can learn from that.


I love working with people who don’t have my background, like the staunch engineers who are on headphones on coding for hours. They typically are not extroverted. When I do get to work with them, I’m excited to learn something new. 


Think about diversity of experience and perspectives, that includes age. Consider the volume of wisdom that you bring to the table that a young person doesn’t have. You can help guide the organization because you likely have a lot of patience that you’ve developed over your lifetime, that maybe some folks younger and career don’t have.”


Onboarding processes often don’t yet exist in startups. How can I succeed?


Tip: In a startup, you get the opportunity to document and make and shape the processes better for the future organization. 


“The onboarding process tends to be non-existent. You have to take the attitude of: “let me grab this, let me grab this, let me grab this.’ and you create the plan. You get to be the author of what will be better for the next person.”


Instead of finding documentation, you may have to sit down with your leader and your team to say I need more context and ask clarifying questions. 


Ask effective clarifying questions & follow-up with gratitude

“ ‘I hear you saying x, y, & z. But I don’t actually understand what that means in the context of this discussion. Walk me through it a different way.”  Then express gratitude for them taking the time to do that.” 


“Try repeating back what you think their intent is. Say: ‘I believe what you’re trying to convey to me is that the sky is purple. Is that true?’ Likely they will say, ‘No, that’s not what I meant at all.’ And you say, ‘Okay, great! Can you try explaining it in a different way? Or can you try using a different approach?’ Then express gratitude for them walking you through it. 


Be curious first. Take action. Save Judgement.

“If you look at a process, and think, ‘this is garbage; it is disorganized; it is not helpful; it is unclear.’  If you go forward with that attitude, you’re not seeking to understand. Someone might be like, ‘Oh, I wrote that in five minutes because nothing existed, please make it better.’ That’s probably going to be the answer in a startup. The answer is probably going to be, ‘That’s just the best we could do at that time; we had four people.’ We don’t have four people anymore, and now you’re here, so please find a way to contribute.”


Can I balance working in a tech company with my life–especially if I have kids or people I support?


Yes – you need to be proactive about setting boundaries that help you thrive.

“If you choose technology, you also have to be intentional about how you support yourself.  


You can’t be the best version of yourself if you’re not filling your own bucket. Your work is going to be less than stellar; you likely are going to get passed up for things like promotions, raises, lateral moves, etc., if your bucket is empty. If you gas yourself out, that’s on you, not the company. 


There have been times where I’ve worked so much that my hair was falling out in chunks or I wasn’t sleeping because my brain could not turn off at night. 


When you work in tech, you need to set healthy boundaries and communicate with other people what’s important to you. 

If you pretend that your kids aren’t a big part of your life, that’s not your authentic self. If you pretend that your cats and dogs aren’t important, that’s not your authentic self.”


Work is only a component of your life. Be intentional about the choices you make.

“When you think about how you balance work in life, know that they’re the same thing. It’s all your life. 


Work is a component of your life. Your hobbies, your children, your cats, or your love of travel are all components. 


If you love traveling, find a company that doesn’t have any offices and is completely asynchronous. Go work from a beach in Hawaii, and nobody cares, although they may be jealous. Your location is not going to affect your ability to impact the outcomes of the business in a remote company.”


What books and resources do you recommend?

  • The Art of Happiness by The Dalai Lama and Dr. Howard Cutler
  • The 5 Dysfunctions of a Team by Patrick Lencioni
  • Turn the Ship Around by David Marquet
  • No Ego by Cy Wakeman