How to Show Up as a Strong Leader… In Good Times and Bad: An Interview With Naeem Ishaq, CFO at Checkr

Naeem Ishaq is no stranger to making career changes during tumultuous times. He graduated college during the dot-com bust, transitioned to a role at Salesforce during the 2008 recession, and now, four months into his role as CFO at Checkr, he’s helping lead the company through the COVID-19 crisis.

During our in-depth interview, Naeem shares how to show up as a good leader during a crisis, and how you can set yourself up for success as your role pivots or expands to include additional responsibilities.

We also discuss the role confidence plays on your team’s performance, the shift to strategic and business-minded CFOs, and the importance of leveraging the experience of other leaders to make sound, informed decisions.

Leslie Boudreaux: First of all, when did you know you wanted to be a CFO? Is it something you’ve always known and been working towards? 

Naeem Ishaq: No, anything but that. I started my career as an entrepreneur during undergrad, and I knew for sure I wanted to work in technology. I was playing with computers at five years old, coding at eight, and building computers at 10. As I got older, I became even more fascinated.

My interests also extended to sociology—including the impact of technology and how it’s helped humanity and society evolve. I knew I wanted to do something that incorporated both of these passions.

And then, from the finance side, I’m a quantitative and analytical person. When we work in finance, we always see the big picture, and I fell in love with that. I ultimately discovered that the best way I could contribute, at least to this point in my career so far, was to be on the finance team.

You haven’t had a traditional path; what do you think made you a qualified and attractive candidate for the CFO job?

Naeem Ishaq
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The thing I’ve done best to prepare myself is to be good at the core. You can’t build a house without a strong foundation. To be a good CFO, you have to have solid roots and control functions of the role; you have to be able to manage budgets and manage investors.

Coming off the dot-com crash and the Enron scandal, the pendulum swung more towards control-oriented people, and most CFOs being minted then were coming more out of the accounting. That has moved dramatically to strategic and business-minded CFOs.

I find that more and more, the thing that separates great CFOs is being a business generalist who can think broadly. Someone who can think about not just controlling costs or reporting accurate numbers, but also how to drive growth, bring new ideas, and drive profitability. As a general leader, you are someone who, if needed, can step up and help support where the company is going.

I also learned so much from Sarah Friar, who was my manager at Salesforce and also brought me on at Square right after she joined there. It was interesting to see her growth at Square, where she was asked to take on so many responsibilities. We were evolving as a business, and she was always ready, capable, and willing to step up. She was a great role model for me.

Were there specific things you took on or ways to become more involved, under Sarah? 

Yes, I’m eternally grateful to Sarah for giving me the opportunity to try new things. To learn, fail, try again, and have confidence that I could achieve great things and that I would get better. Some of those were at my request in pushing to do new things, and in other cases, Sarah would ask me to step up and take on new things.

For example, a couple of years in, we did a big reorganization across a lot of service teams. Our risk org, which was one of the core functions of the company, lost its lead and she asked me to take on responsibility for that team. It’s a huge team—very critical and high-impact—and I had literally zero experience in risk management.

So, I had to learn that on the fly and it took a lot of faith for Sarah to trust me to take on something that, if it breaks, could completely derail everything the company does. I’m very grateful for her confidence. It allowed me to grow, and I’m proud of the work we did together to help that organization improve the results of the company.

I feel like going forward, people are going to be asked to do more, without necessarily giving up the responsibility they currently have. How would you think about that?  

Well, the first thing that comes to mind is to prioritize and be ruthless about where you spend your time. I’ve found that all the great leaders I’ve worked with have all been excellent at prioritizing what they’re doing and what they’re not doing. Setting clear expectations about that is so important.

Second, business is a team sport. So, in the example I mentioned earlier of taking on the risk leadership role, I had to ask my other lieutenants to step up and do more to enable that, and trust that they could.

“I find that more and more, the thing that separates great CFOs is being a business generalist who can think broadly. Someone who can think about not just controlling costs or reporting accurate numbers, but also how to drive growth, bring new ideas, and drive profitability”

The hard work and investments of building a great bench pay off because it allows everyone to step up, as you’re required to step up. Without the luxury of having great people around you, that would not be possible. The investments you make one, two, or three years beforehand, definitely start to pay off. So, always take a long-term view in terms of doing the hard work to not just settle on okay talent, but extraordinary talent. The payout there is unimaginatively positive.

You mentioned being given the opportunity to grow and do things that you’ve never done before. Do you do that with your team as well?  

Yes, certainly. That’s one of the hardest things about leading is knowing how much rope to let out; knowing when it’s too much and when it’s too little. It’s not easy and it’s something I’ve gotten wrong in the past, but have improved my judgment over time.

But yes, I look to my superstars and give them a chance to step up and take on more, even if it’s new, uncharted territory for them. Everyone, at some point, does something for the first time. So, if you are careful to not set them up for failure by giving them too much, then usually that works out really well.

I feel like this piece is the secret sauce of management and leadership, knowing when is the right time to empower someone and also being willing to give up control yourself. Setting them up for success and letting them learn from their mistakes, but having a safety net.

Well, one thing that might be interesting is a book called The Leadership Pipeline. I was turned onto this book pretty early in my career by a gentleman named Dan Delmore, who was my last  manager at Intel. He was also a lecturer at the local university and a very thoughtful leader.

The book walks through different career transitions and covers not just how your behavior has to change when you make the move from individual contributor to first-line manager to ultra-leader—but, more importantly, how your values have to change as you make those transitions.

It was really eye-opening for me at the time and continues to be one of the books that, every time I make a transition, I go back and reread the passages to remind myself.

I remember there’s a phrase in there that scared the hell out of me when I first read the book. I was on the cusp of hopefully becoming a people leader, and it said, “Often the best individual contributors” – which I was at the time – “are poor managers.”

I just thought, wait a second, I’m a high-performing, individual contributor, does that mean I’m going to make a poor manager? And it was a wake-up call that this is not just going to come naturally, you have to prepare yourself, and it really got me to take that seriously. So, by the time I had the opportunity to be a people leader, I felt like I had already spent a decent amount of time reading and learning about it.

I think something else that helps is paying attention beyond your narrow focus at the moment. Look around you, see what other leaders are doing, and put yourself in their shoes. If you see a major decision being made, ask yourself, What would I do? and then go back and check whether you were right or wrong. That’s how judgment is built. Often people say, ‘’You should learn from your mistakes.” You should, but you can learn from everyone else’s as well.

What advice have you been given that’s been impactful for you? 

One of the things I learned from Dan was when leading people, you should speak to them as though they are capable of achieving the greatest results you can imagine, even if you aren’t sure they can do it. So, you might see someone who you think is just an okay performer, but you coach them as if they are an absolute rock star and they have the potential to achieve those high outcomes.

I didn’t understand that at first. But if you think about it, and actually in practice, I found that by helping them to see what they’re capable of, you’re giving them the confidence to try a little harder, above their current bar of expectations.

I’ve been shocked how often people have exceeded my expectations after doing this. You just have to start by actually talking to them as if they can do it.

So, say somebody working for you was not performing at the level you needed them to be, and then by telling them that you expected they could do great things, they didn’t just meet that expectation, but blew past the expectation and exceeded it? 

Yes. I’m telling you, it’s a majority of the time, which is hard to believe. If you can give them that little vote of confidence and show them what that looks like, that might enable them to try to go for it.

The times when I haven’t done that, I think people generally wallowed in whatever level of performance they were already at.

People are amazing. But they have to be shown what good looks like and how to aim high, and they have to have self-esteem and self-confidence in order to try.

That says a lot about the power that confidence plays on people’s performance.

Enormously. It’s unbelievable just how important that is. Confidence matters a lot. I think as a leader, demonstrating belief and inspiring people to do great things, setting proper expectations, and raising the bar all work well. The best part about it is everyone wins. Obviously, you win, because as a leader, you’re getting more out of your team, but they win because they’re doing better, the company benefits from the increased performance, so everyone wins, all by a little bit of faith.

I’m curious, do you subscribe to the school of thought of maximizing somebody’s strengths versus focusing on weaknesses?

Absolutely, yes. 100%. To focus on weaknesses, that is not how the world works. Of course, there’s a minimum threshold that’s required in some other areas that you augment. But I think you should find what you’re really good at and double down on that.

I’m not going to be the greatest CFO in the world by being the world’s greatest accountant – that’s not my strength. Hopefully, I’ll be the best strategic thinker, the best planner, and the best investor manager, which is where my greater strengths lie. I have to know enough to be dangerous and to be able to rely on experts who know much more than I do about those other things to augment my own capabilities.

Let’s shift gears a little bit and talk about what’s going on right now. How do you feel like your role has changed since the COVID-19 outbreak?

When you are in a crisis you have to change your priorities. You have to certainly think about, first and foremost, how do you protect yourself, your team, your employees, your company, and your community. In this case, they were all related.

Your time orientation also has to change a bit as well, and I think you have to be more directive and make faster decisions than you’d make otherwise.

If you’re in a burning theater, it’s better if somebody yells, “That’s the exit we’re all going to take,” than to sit down and deliberate which one to take. Leaders have to be a lot more directive in a crisis and there are many things where you have to just be willing to make the call. You have to use your best judgment, and you have to move fast.

“Values are easy to espouse when things are easy. They’re really hard when they’re not. You have to test whether those truly are your values as a company and as an individual.”

Then, once you ensure that you’re protected, which includes: your cash and your burn rate, the focus shifts to the health and safety perspective, how are people managing, succession planning, and God forbid if one of your team members gets sick, who’s in charge? What do you do?

I’ve been so amazed by how our team has come together to pull these things and bring them forward very fast. We’ve also been very fortunately on the leading edge of taking action as a company. Checkr was one of the first companies nationally to shut our offices and bring everyone remote, way ahead of most other companies.

When you talk about preparation, fortunately or unfortunately, it’s not my first rodeo. This is now the third crisis I’ve managed in. I graduated college in 2001, when we had the dot-com bust. I transitioned from Intel to Salesforce in 2008 just before the Global Financial Crisis. I transitioned here into Checkr in 2020 a month before COVID-19.

Maybe it’s your destiny to make big changes during tumultuous times.

No, kidding. When people talk about these tumultuous times, they’ll talk about 1997, 2001, 2008, and 2020. The current situation is clearly going to be remembered for decades to come. So, yes, I’m trying to leverage my own experience and the experience of other leaders to allow me to make good, sound, informed decisions. It really does test a lot.

The other hard part about it is that, in times of crisis, you have to make some very hard decisions, and it will put your values to the test. Values are easy to espouse when things are easy. They’re really hard when they’re not. You have to test whether those truly are your values as a company and as an individual.

We spent a lot of this call talking about leadership and how to show up as a good leader. I feel like it’s so critical now, more than ever, when times are bad versus good. 

How do you think about that messaging to strike the balance of being authentic and honest, but also supportive when we don’t really know what the future holds.

Yes. It goes back to this point of values. So one of the values we have in Checkr is transparency. Again, transparency is easy when everything’s great. It’s hard when things are not so great.

Fortunately, Checkr is in good shape so far, but we’ve been very extremely transparent with the hard truth, which is, we just don’t know what the future holds. This is completely unprecedented in anyone’s lifetime to see something like this.

The last time we had a pandemic like this, the world was a completely different place. We also don’t know the extent of it – everything is so uncertain. So, I think being honest with people about how we’re prioritizing, how we’re thinking about managing cash flow, everything about making trade-offs, and recognizing leadership teams. But there’s a cost to that transparency as it places an extra burden on all employees. I think that where companies go wrong is when they’re partially transparent. Because when you’re partially transparent, and you are not authentic, people are really good about sniffing that out. They just know, people are intuitive. But really, it tests us to see whether or not we can live up to our values and maintain transparency.

So far so good, we’ve increased communication. We’re now doing all hands, virtually, with the company twice a week to keep people abreast of where we are and what’s happening. We’ve already taken some actions to shore up our costs a bit as well, and everyone supported and is behind that, too.

We’ve been honest with people that we don’t have all the answers right now, but here’s the framework we’ve built, and here’s how we’re thinking about it. People generally understand that’s all they can ask for, and we can’t promise more than we can deliver. Their reception so far has been positive.

What are you excited about for the future?

I’ll start at the broadest level. Humanity always finds a way and this too shall pass. It’s amazing that we can deal with insane adversity and still wake up the next day and still find an opportunity, see the sunshine and smile. So, I know we’re going to get through this, like we always do. I’m looking forward to seeing that day when society just functions again. That’s the thing I’m most excited about.

For our team, the most heartwarming thing I’ve seen is how much everyone has banded together during this crisis to support each other, and to support our community means a lot. The work that we do at Checkr has a very real impact on people’s opportunities to find work, and especially when a lot of our customers focus on the gig economy. In many cases, that’s the only work they can find. I’ve been inspired by how much I’ve seen my colleagues step up and support that. I’m very excited about us continuing to accelerate that for the duration of this crisis as we come out on the other side.

On a personal lens, again, I feel very blessed. I’ve had amazing opportunities and I’m excited to continue to grow in my career. Moreover, seeing some of the great leaders I’ve had a chance to work with, to mentor and to groom, to see them grow and now seed a lot of the value, it has been incredible and very rewarding.

That’s the part we always look back and we remember the most. When we get through this crisis too, we need to look back at how people showed up as human beings through all this.

Yes, I couldn’t agree more. Thank you. 

Thank you.

 Featured Image: Checkr

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