Alisa spends most of her non-working hours with her pup.

Alisa spends most of her non-working hours with her pup.

on going after your target position and keeping your eye on the long game


A mutual friend connected me with Alisa Frederick (Kate Brown – go read her post if you haven’t already!), and I’m so grateful that she did. Like Kate, Alisa is a bit of a unicorn in that she is one of very few women in a very male dominated world—Alisa works in finance. She is a Partner and Managing Director at Caltius Structured Capital, a firm that provides subordinated/mezzanine debt, minority/structured equity, and unitranche solutions for middle market companies. (Is it obvious that I just copied that explanation from Alisa’s LinkedIn? I don’t know what most of those words mean, but essentially, her company invests millions of dollars in businesses to facilitate things such as buyouts, recapitalizations, growth, and acquisitions.)

In addition to being a powerhouse finance exec, she also happens to be an incredibly thoughtful, kind, and self-aware individual that is generous with her time and wisdom. During the course of our long brunch together, she shared enough career lessons for a few blog posts, but I chose my favorites to share with you here. I hope you get as much out of them as I did.




Although Alisa has been in the finance world for many years—nearly two decades just at Caltius—Alisa revealed to me that earlier in her career, she never would have imagined that she could be a partner at a private equity firm. She didn’t even study finance in college! She graduated with a political science degree, but followed her interest and applied for a bank credit training program in NYC. She didn’t have the right qualifications on her resume, but she went for it. When the interviewer asked her what she would contribute to the role, she responded, “I can write well and I’m good with people.”  As it turns out, that was the ticket. They knew that they could teach her the banking credit and leadership skills, but her other skills were seen as particularly valuable.  

Alisa told me, “It doesn’t really matter what’s on your resume. If you see a position that excites you—go for it.” This urging reminds me of the research that revealed that men will apply for a job if they feel that they fulfill 60% of the qualifications while women won’t spring for the role unless they’re confident that they meet 100% of the requirements.

We women have a terrible habit of closing the door on ourselves before we even try and walk through it. We make the [often false] assumption that we will be found wanting, and instead of letting the interviewer be judge of that, we eliminate ourselves from the running without giving ourselves a real shot.

There are three things that employers assess when going through the interview process with a candidate: 1) qualifications, 2) desire, and 3) fit. Notice that being qualified is only one factor that they consider. Especially earlier in your career, culture fit and a desire to do the job are often weighed much more heavily. So, be a little bolder and apply for those roles that excite you.

Sure, Alisa also recognizes that there are roles and industries that really won’t give you a second look if you don’t meet their criteria, but she makes a good point here as well: It’s still worth putting yourself out there. The process of reaching for the role may be what forces you to take a look at where you are and make necessary adjustments if that’s really where you want to go.



For many young ambitious women, the overthinking and self-doubt doesn’t stop once we’ve landed the job. Alisa was telling me about some mentorship that she’s done with young women in the business program at my alma mater, and she reported that many of the young women are just panicked. Everything feels so high-stakes to them when it comes to their careers.

I love Alisa’s perspective on this. She says to “recognize the longevity of your career and all that you have ahead of you. Look at each little thing ahead of you—each ask, pitch, project—in the perspective of your career. It’s just so immaterial. Not everything is a throw in the towel moment.”

In Alisa’s career, there have been countless times that she could have fallen apart if she hadn’t had this perspective. She’s responsible for winning business for the company, and there are dozens of deals that she loses every year. Fortunately, she recognizes that winning or losing those deals has very little to do with her. Not everything is going to be a win—or even needs to be.

She illustrated this concept by comparing it to a game of golf. You can hit some terrible shots and get a really crappy score on a hole, but then—you get to choose whether or not you take that with you to the next hole. What’s done is done; that next hole is still waiting there with a new opportunity for that hole-in-one. 

In the long careers that we can expect to enjoy, there will be things that go wrong. We will make mistakes or poor decisions that have consequences, but it’s what we do in those moments that matter. Our thoughts about these situations have the power to stall us in our careers, or allow us to keep pushing on and growing. It’s important to keep the mindset that we can learn from these experiences and know that there’s always the next “hole” (or project, or client, or pitch…) that we get to take another shot at.

This is called resilience and persistence, and it’s critical for achieving all that we hope for.


Another antidote to the anxiety and self-doubt that so many of us experience is to get clear on the skills and perspectives that you bring to the table that provide value in your team or organization.

Earlier in Alisa’s career, she was insecure because she thought she had to emulate her male peers and be a “schmoozer” to win business and grow her realm of influence. But, through time…and trial and error…and self-reflection, she found that the way that she can provide the most value is by doing what comes most naturally to her. Her team needs her to show up the way that she does best. She’s not flashy or loud; she balances her team by being the thoughtful listener, the one attuned to her clients’ needs. She’s a trust builder. She’s the level head in the room that helps her and her partners navigate tricky situations.

It’s a beautiful irony that it’s actually the things that make her different from her male peers that make her most valuable to the team and company. At a certain point, she started to see herself in that role, and the insecurity started to melt away. She told me, “The result would have been so different without me,” and that’s where she puts her focus.

Finding your unique value is a quest that involves paying attention along the path of our careers to find the confluence of where our skills and what energizes us creates the greatest impact in the organization that we work in, and then continually working to flex and grow those.