How Do You Know When to Take Career Risks?

(Photo credit @claybanks)

Venture capitalists are by definition investors who take calculated risks, and usually really, really big ones. Their goal is to invest in multiple companies with the assumption that the majority of them will fail, but at least 1 out of 10 will yield 10X or higher results (which will hopefully make up for the failed investments). They spread the risk out. They listen to hundreds, even thousands of startup company pitches and select the ones they think have the best chance of success, after evaluating the company’s management team, the financials, the tech’s potential, etc.

And even with all the resources at their disposal, they get it wrong ALL the time.

So please don’t think you have to have everything figured out completely before you decide to take a career leap. And know that you’re going to make some mistakes along the way - but that’s ok!!

Let me offer you some tips and strategies to help you with this type of career decision-making.

With VCs being taken in by the hype, how can you avoid joining a leaky ship (aka a bad startup)?

• Try thinking of making career changes as taking calculated risks. For some, it’s helpful to think of a chess game. How many moves ahead can you plan out and how does that help you decide what to do today? When/how do you need to shift strategy when your “opponent” throws up a surprise move (aka a life change, an industry shift, or an economic downturn)?

• Learn to identify your risk tolerance. I talk often with students/clients about identifying your ‘risk tolerance.’ Everyone has a different way of assessing risk in their career and in figuring out how much risk they can handle at any one time. Remember, it can also fluctuate based on your age, family dynamics, finances, etc.

  • Check out this article for more details on the RRIS method for improving your risk tolerance.

• Face your fears. You can also work to increase your risk tolerance by trying this fear-setting technique from this famous guy Tim Ferriss I knew in college.

  • The aim of the exercise is to name your fears so you don’t let them lurk in the shadows and prevent you from taking big actions. I was surprised by how helpful it was the first time I did it, that even though I scared the hell out of myself, it felt great to vocalize my fears and face them!

  • Here’s another take on this fear-setting exercise too.

Another way to make hard career decisions is by educating yourself so you aren’t leaping blindly.

• What universal skills do you have? You can educate yourself about your skills by taking assessments like StrengthsFinder.

• Learn about the startup landscape. You can also use some of the tools the VCs do to educate yourself about the startup landscape & specific niches within it (fintech, 3D printing, IoT, etc): CBInsights and VentureScanner.

• Get recommendations on top startups to join. Wealthfront also does a yearly career-launching companies blog post, and provides great criteria/methodology for how to choose among one of these organizations.

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Want personalized career guidance? Take a look at my Career Strategy Session options.

How to get ahead in an interview

(Photo credit @charlesdeluvio)

You’d be surprised at how many candidates don’t take the time to do the following — and how much value each of these items will provide in any interview situation.

1. When looking to work at any tech company, understand how they make money. 

   • Learn what their business model is, even if at a high level. Here are 53 of them to check out! 

   • For startups: many funders have changed how lenient they are with companies that burn cash for a long period of time without generating revenue, so be aware of how long the runway is for newer startups. Great article on this: How To Vet A Venture-Funded Startup

   • For larger companies: aim to find a role within the money-making part of the company FIRST. Then, once you’ve had success there, it’ll be easier to pivot into another part of the company. 

2. If you’re selected to interview, fill out this template to help you understand how the company works & makes money. 

   • Business Model Canvas template

3. Use that information to answer interview questions with more depth and to ask insightful questions about the company’s growth/stability. 

   • This will help you with interviews for *any* type of role at a tech company and will put you miles ahead of most other interviewees who didn’t take the time.

4. Prepare for the variety of ways that you will be interviewing in your job search.

   • Phone Interview Tips From a Career Expert That'll Get You to Round Two

   • How to Succeed in a Virtual Interview

   • Consider using 1-2 post-it notes as strategic reminders. Maybe you always forget to give results in your PAR answer? Write down the PAR framework on a post-it (Project Action Result) to help you. Just don’t have too many post-its - or you’ll look at them and not your interviewer!

5. When preparing for interviews in tech, one technique that requires a lot of preparation is “disagreeing tactfully with your interviewer.” 

   • This HBR article does a great job of describing 4 steps for how to effectively employ this interview technique: do your homework; give yourself space to think; ask permission to speak candidly, and trust your instincts. 

   • Use this technique because you operate well in a company culture that appreciates discussion & debate. (The best part of the CareerLeader assessment is the MyCultureMatch section. In this sample pdf result, check out pages 13-16 to see the 4 main types of company cultures and see which one(s) align best with your preferences.) 

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Want personalized interview tips and career guidance? Take a look at my Career Strategy Session options.

Handling job searches in tough times

(Photo by @andrewtneel)

As I meet with students, I am hearing a continuous stream of questions: "what do I do? is this going to get better? how do I handle it? what will happen next month/year?" I try to be as honest as I can in my assessment of the hiring landscape, and share my story to show that you too will face challenges in your career and figure out ways to recover.

Can I tell you a secret? I've been laid off three times in my career.

Once, in early 2001: I have the dubious distinction of being one of the first people McKinsey ever laid off. As a junior recruiter, I started my job and was there for 6 weeks before getting laid off in early 2001. I then received 6 weeks of severance and 6 months of outplacement services (which is what senior executives received at companies like JP Morgan and Ford). At the time, that meant a personal career coach and a dedicated office in midtown Manhattan to help support my job search. Luckily for me, the outplacement firm then offered me a job -- and that's where I was working on 9/11/2001 when tragedy struck New York City. My job was the only secure thing in a world of chaos and fear, and I believed that my work was helping others who had lost their jobs recover and move forward.

Second, in 2004: I was excited to join a social networking startup called TheSquare.com. As Director of Marketing/Membership, I hosted parties to get new members -- and when actors Chris Noth (Sex in the City) & Scott Speedman (Underworld) attended, membership skyrocketed 30%!! Things were going great! And then we started cross-promoting with this tiny college startup called TheFacebook...and within a couple months, I was laid off. It took me a few months but then I landed at MIT to help grow a preprofessional program called UPOP. I loved helping students gain skills to get their foot in the door & launch their careers.

Third, in 2007: I was poached from MIT to start a campus recruiting program at growing B2B startup Endeca. I worked with the CEO and senior leaders to build a program to hire coders & consultants as intern and full-time hires, managing $.5M budget ...until the company started to see a sharp decline in sales as the mortgage crisis turned into the Great Recession. I was offered the chance to stay on in a regular HR role but I enjoy engaging with students more than benefits administration. I landed my role at Harvard Kennedy School a few months later and had a front-row seat to the Obama election. I worked for David Gergen, a former advisor to 4 US Presidents, and helped connect graduate students to senior leaders in healthcare, government, education and business - from General Colin Powell to Bill George (former CEO, Medtronic) to Valerie Jarrett (former senior advisor to President Obama).

Why am I telling you this?

I know what it's like to have hard things happen and to not know what to do next.

I know that it can feel like the wind is knocked out of you.

I know what it feels like to not be sure how you'll pay your rent.

I know that we are facing something unprecedented in our lifetimes and that's scary for everyone.

Leaders we admire face all kinds of challenges on a daily basis and all of them started right where you are.

I know that you have the skills and the initiative to figure out a way forward -- and sometimes, really great things can come from uncertain times.

This too shall pass.

I was able to bounce back from each of these challenges by trusting my skills, my instincts and my network.

Many organizations are full of good people who are trying to do the right thing by their employees, customers and future candidates (though there will be some who make a lot of mistakes along the way). There is an incredibly generous spirit out in the world right now - try to tap into it or add to it if you can.

#WhatShouldIDoNow

• Take a deep breath. Exhale. Repeat until you are calm. Trust me. It will get better. You are amazing.

• Practice empathy towards others. Imagine what it is like to be in their shoes and let that guide you in your responses.

• Build your resilience. My post last week was full of tips on how to cope & how to build your resilience.

• Look to see who is hiring.

  • 28 Companies that are Hiring Now

  • Umbrella is hiring immediately for an Operations Partner to help provide services to seniors who are stuck at home. Let me know if you want to be connected.

• Stay in the process. Continue to keep networking to find out about job opportunities before they are posted. And keep submitting job applications - the only way for you to be considered is if you have applied.

• Ask for help when you need it. Family, friends, colleagues, etc are all great resources to help you with problems big and small, or seek out professional support for the challenges that require more focused attention.

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Want personalized job search strategy tips and career guidance? Take a look at my Career Strategy Session options.