Women in tech need to get comfortable asking the hard questions and taking risks. Here's why

As a woman working in technology, it’s not always easy to make your voice heard. This wasn’t the case at the recent Acumatica Summit in Seattle, where three women tech leaders gave open and honest accounts of how they’d climbed the career ladder in this male-dominated business.

The panellists shared their advice on several areas where women traditionally can struggle in the workplace. One of these is self-promotion, advocating for themselves for new positions or opportunities, which we covered in part one of our coverage. Another challenge is becoming comfortable with asking for what you need, whether that's pay, support, flexibility or resources.

To overcome the difficulty associated with making an ask, Helen Yu, founder and CEO of Tigon Advisory, recommends putting yourself aside and instead focusing on the value alignment. Yu cited an example of asking for additional resources on a team:

What I do, I’ll go to the sales leader or CRO to say, what hinders growth? Because the team is not outperforming, and then he'll say, we wish that we can have the reporting faster, because it takes 10 days. I said - what if I can drop it to two days? But here's an additional cost, I need to find new resources, my department cannot fund the entire cost, can you chip in half of the cost? So that becomes a very easy conversation.

You must think about how you tie whatever ask you have, to that strategic value. And then find the partner who can really help you achieve that goal.

Conflict resolution

Growing up in a household where there wasn’t much conflict meant that Stephanie Valenti, VP of Sales at FinTech BILL, lacked the confidence to have the awkward conversations at work. Whether negotiating an offer letter or responding to a sales person stealing her lead, she would rely on someone else to deal with the situation on her behalf. Valenti says:

I didn't have that confidence or ability to go over to my peer and say, you stole my lead. I would run into my manager's office and be like, she stole my lead, handle that for me.

Things changed when Valenti was about to get her first manager role, and was going through the interview process. Her manager pulled her in and told her to go handle the situation herself. She adds:

I don't want to have that conversation. And guess what? I had the conversation, and I am living today, I made it through. That one conversation that I was forced to have fueled every other uncomfortable conversation that I've had since.

Nowadays, if you asked her team whether Valenti is bold, asks for what she wants, and is loud in a room, they would answer that she’s probably one of the most direct people on the leadership team. She adds:

But I did not start off that way, and so my guidance is, try. The more you practice, the more it becomes comfortable. You do not have to grow up with that. It does not need to be innate. It can be learned.

As a 24-year old starting out in public accounting at KPMG, Shary Dye, Major Partner Account Manager at Acumatica, similarly was lacking in confidence. The first audit they signed her up for was to a Fortune 100 company. She recalls:

I was here terrified, and the senior manager on the account said, 'You need to go in and talk to the CFO and ask the questions about the variances'. I said, 'No, I'm brand new, I can't do that, this is a big company'.

The reply was something that has stayed with Dye throughout her whole career. She was told:

This is your area, this is what you're in charge of, this is your area of expertise, do not be intimidated that the CFO may know all these other things. This is your responsibility, and you can do this, you're the expert of this thing. Go on in there, you can do it'.

While Dye was still frightened and couldn't make eye contact with the CFO, she got through the experience.

Now I live with that, that I deserve to be in the room, the thing I am there doing or talking about, or the conversation that I'm having, I'm the person that's supposed to be having it, and I deserve to be there.

Role reversal

Taking big risks is something the panellists agreed is crucial for progressing women’s careers. For Valenti, this centered around her role at home. As a mother of three, Valenti and her husband made a decision early on in her career that her husband was going to be the one that stayed home if she was going to climb the career ladder. She notes:

In my house, we have reverse roles. There's no magic answer where this is a perfect balance for you. I weekly do a lot of reflection. I look at my week and I'm traveling, my husband's doing all of the hard work. And so this was corporate Stephanie week, it was zero family week. When I look next week, my hope is that maybe my split is 50/50. Maybe I was really there for my children and my husband, and then maybe it changes again the next week.

Whatever type of week it’s been, Valenti was keen to reiterate that she’s not hard on herself; she doesn't set herself a goal for each week because she could end up letting herself down. She adds:

The goal is just being mindful and monitoring, and if there's something I'm not doing enough on a recurring basis, is having a real nice conversation with myself about what am I going to change to change the outcome.

Allowing herself to be the same person in her corporate and personal life was the big risk Dye took. She explains:

It's exhausting to live two different lives. At home, I get to be vulnerable, and I get to be Mom, and I get to do smiley emojis, and then I would move into my work life, and I have to be serious. I work with all men, I have to be masculine, I have to be tough.

It took a long journey to get there, but when Dye finally gave herself permission to flip that and embrace being feminine and vulnerable in her career, she felt so much freer.

Being strong and austere is not better. I leaned into being feminine and vulnerable and smiley emojis, and xoxo in my emails, and proud of it. That freed me up so much. It didn't take all the workload off, but I was the same person in both sides of my life, which really I had no idea how much that dragged me down.

Lessons learned

Looking back over her career so far, one thing Dye wishes she’d known earlier is that she’s a survivor. She explains:

The times I get into my head and wondering, 'Can I do this? Should I do this? Should I take this job offer or that job offer?'. Make a decision and go with it, and I need to trust the fact that, every time something has changed in my career and in my life, I managed to make it work. I'm still here, and I have to trust that I'm a survivor, and I've always found a way to success, and I'll do it again.”

Don't jump into reacting to sudden events, whether that’s in her professional or personal life, is something Yu has learned. Instead, take a deep breath, think about what’s happened, consider the options, and work out what's within your control and what’s outside it. She adds:

Focus on areas that were in your control and trying to work on those. If it's outside your control, leave those there, don't waste your time dealing with things that are out of your control.

Valenti recalls a tip a CFO shared with her, that when dealing with a risk or something she’s anxious about or uncomfortable with, think of the absolute worst outcome that could happen, and then write it down. She says:

Every risk that you're thinking about or you're stressing about or you're anxious about, probably doesn't have an outcome that's all that serious. Write it down and just remember, take those risks. It's totally worth it