Searching for your career next step

Over the years, I’ve collected some exercises and advice about navigating career next steps. I’m finally packaging it up.

Is it time for something new?

Maybe you know that you need a change, or maybe you just know “this isn’t it” when it comes to your job. Sitting with these two phrases can be a litmus test to see if you’re ready for something different:

• You should never be somewhere that makes you feel small. (Listen)

• You should never be in a place that doesn’t bet on you. (Read)

If these statements pulled on you a bit and made you question where you are, it’s time to start examining if a change is the right answer.

Do you need a Small or a Big Change?

A “small change” is one that can take place in your current work environment. Small changes can have a big impact, and if you know what you need, you might be able to turn a problem into an opportunity. A “big change” might require you to drastically reimagine what you’re doing and who you are, and might have high switching costs.

To evaluate if you need a small or big career change, ask yourself the following questions:

1. What do you think needs to change?

2. Do you have the energy to fix it?

3. Do you have the power to fix it?

If you don’t know what needs to change, sit with question #1 as long as you can and compare notes with others who might be in similar circumstances.

If you answer No to either #2 or #3, the next thing to do is to make a big change.

If you answer Yes to both #2 and #3, you’re eligible for a small change, but give yourself a timebox (I recommend 3 months). What needs to be true at the end of your timebox in order for you to be happy? Write it down. Set a calendar invite with your criteria, and revisit at the end of your timebox. If your criteria are met, you’ve just made a successful small change! Congrats! If your criteria still aren’t met, then it’s time for a big change.

The nice thing about this exercise is that it forces you to be concrete. Chances are: your leadership team wants to help you; they just might not know how to do it.

Getting Concrete about a Small Change

Ask concretely for what you want; your team or manager can always say no.

Things I’ve seen folks successfully ask for to improve their lives without having to make a big change:

• Change of scope or responsibilities - You can change your role entirely, or ask to offload the least enjoyable parts of your job to someone else. It might turn out someone likes that work more, or it creates an opportunity for someone else to take it on.

• Change of hours - Many managers want to hold onto talent, even if it’s for fewer hours.

• Change of location - Especially with more reliance on video conferencing, location is much more flexible.

• Change in title or pay - Your manager may have no idea that you are unsatisfied with your pay or title. Make sure you mention your goals to them.

• More support - Sometimes, you just need some more staffing. It could be asking for admin support, asking for more headcount, or asking for more money to hire vendors.

In some cases when I thought “I need a change”, I found that it was me that needed to change. I strongly recommend everyone listen to Leadership and Self Deception. It’s told like a story and is only 4 hours. I haven’t met one person that regretted listening.

If you get to the end of these exercises and you have more confidence that you need a big change, read on.

You need to be healthy before a Big Change

One of the best pieces of advice I’ve ever gotten was that you should be running towards something, not running away. During one particularly bad period of burnout, I realized that even if I found something great, I probably couldn’t identify it. I needed to heal before I could run again. These steps helped:

• Get active, eat well and sleep - My wise Chinese grandpa always used to say, “If you don’t have your health, you don’t have anything.” When I’ve reached a point of burnout, I inevitably have neglected my body, too. There’s lots of evidence how lack of sleep can make you depressed, and good food and exercise are mood boosters. If you’re struggling to get enough inertia to move, I’ve found Pokémon Go really helpful in building a walking habit.

• Get a therapist - A trained professional can guide you back to a place of empowerment.

• Be kind with yourself - It takes time to heal. Don’t judge your progress. Surround yourself with friends and fuzzy things.

• Take time away if you can afford it - Many tech companies offer paid leave or sabbaticals. Or sometimes it’s just taking a day or two for “vacation” to do the work of healing. If you can’t take vacation, see if there are folks in your support network that can support you to take some “me” time. They will probably be delighted you asked.

• Identify what makes you happy, and cultivate it - These books helped me when trying to get out of a funk:

  • Before Happiness - A number of the exercises in this book illuminated what was and wasn’t impacting my happiness and allowed me to take control.

  • The Life Changing Magic of Tidying Up - It helps you declutter your stuff, but also a good philosophy around where you put your energy.

  • Life Plan Workbook - I’ve done the “Exploring You” section at two major junctures in my career, and found out new things about what makes me happy.

• Know that it isn’t you - Experiencing gaslighting, morale injury, microaggressions and stereotype threat are unfortunately commonplace in many industries, but they are never the fault of the victim. Folks from minority backgrounds also don’t get as many sponsors, so a career plateau is more the function of systemic prejudice than lack of individual talent. Feeling burnt out and stuck? It’s not your fault.

Sometimes it can take a few months, maybe a few years to heal. Just make sure that when you start searching for your next gig, you need to advocate for yourself. It takes strength and centeredness to do that.

Search for Person-Problem Fit

Now that you’re healthy, it’s time to start thinking about what’s next. I like the framing of “Person-Problem Fit” that I first encountered in this blogpost rich with exercises. There’s no right way to arrive at this, but it is a lot of work. Below are some resources that I’ve found to be helpful for myself and others over the years (many thanks to those who have shared these with me 🙏):

Figuring out the What

Any combination of these exercises might help you narrow in on what you want to do. The key thing is to give them your full attention, and then marinate on the work you did. The answers will eventually come:

• Complete the full Life Plan Workbook - Writing down 100 dreams was hard, but the last 50 was where the magic really happened. Only once I was able to get the superficial goals written down was I able to extract values-driven dreams that helped guide my decisions.

• Keep an “Inspiration Log” - Write down all the things that inspire you: a news article, an image, a poem, a song, a conversation with a friend. Then pattern match.

• Keep an “Energy Log” - Track day-to-day what gives you energy and what takes it away. Many books have recommended this in various forms: Designing your Life, Genius Habit, and the Person-Problem Fit blogpost.

• Ask yourself what you hold inside - Spend a day without your devices and write down the answers to the following questions. Don’t worry if you don’t know all the answers, what’s important is writing down your reactions to the questions and everything that might come to mind. Reread everything you wrote a couple weeks later, and see if anything changes or you have more clarity:

  • What do you fear? What takes away your energy?

  • What inspires you? What gives you energy?

  • Where do you want to be in 2 / 5 / 10 / 20 years?

• Take some classes and do some interviews - A class or an interview can be a great way to explore an idea space. Even if you hate it, ask yourself why and use the experience to guide your journey.

• Things to avoid: Common advice that I’ve seen lead towards the wrong conclusions.

  • The “write a book” goal trap - Many people want to have written a book, but not many people want to spend hours a day writing. Don’t focus on the end accomplishment as the goal. Focus on what you’ll enjoy doing for hours and hours every day.

  • The skills trap - Orienting your next step towards building abstract skills is a red herring. If you find something you’re passionate about, you’ll develop the skills you need to succeed.

  • The strengths trap - There’s a lot of career advice out there about identifying strengths; it can lead you astray. Even if you’re good at something doesn’t mean you’ll enjoy doing it.

Figuring out the How

Once you know what you want to do, then the next step is figuring out the stepping stones to get there. Here’s some general advice to keep in mind, but make sure you don’t jump to this step too quickly. It might be tempting to start solving, but you’ll only be charting a course in the wrong direction if you’re not solid yet about your next step.

• Break your goals into smaller subgoals - Celebrate mini-successes early and often. Ride the momentum to your next win. Conversely, if your goals aren’t broken up small enough, the goal might start to feel unachievable.

• Build in accountability and rewards - Find an accountability buddy to share your progress with. Treat yo’ self when you reach a milestone.

• Build in a tripwire to reevaluate - From the book Decisive, I’ve fallen in love with the concept of tripwires. A tripwire allows you to run in a direction, but gives you an opportunity to check to make sure things are on track before you run too far in the wrong direction. A tripwire can be a timebox, but can also be something like “my personal savings can’t dip below $X”.

• Financially plan for your dreams - Finances can either be an enabler or a goal. Find someone to help you (like a financial advisor) or look for grounded advice. Here’s the best article I’ve found so far about how to build wealth.

Finally: You are awesome. You can do things that no one else can. Once you figure out what you were meant to do, run towards it as fast as you can.

Designing Inclusive Products - Deck from Product School on 10/19/17

I had the opportunity to present my thoughts about designing inclusive products at Product School. Below is the video of the presentation, and I’ve also shared the slide deck in case you’d like to click on any of the references.

Move from “checkbox diversity” to valuing a “diversity of perspective”

Over the last three months, I’ve been collecting the insights and opinions from an amazing community of friends and colleagues from underrepresented groups in Silicon Valley. This post is the first of a series about the results of those survey results and conversations.

What does diversity-in-tech even mean? Some say it’s about having more gender diversity, racial diversity, socio-economic diversity, and more. I believe the current way Silicon Valley talks about diversity captures these categories in the form of checkbox diversity, which can alienate members of a diverse team by undercutting their value as individuals. I’d much rather we change the conversation to advocate for a diversity of perspective.

Tech companies use checkbox diversity when they approach building diverse teams by assigning individuals to specific categories and analyzing percentages. Google’s diversity statistics or Etsy’s diversity statistics, for example. Checkbox diversity holds teams and large organizations accountable for fair hiring practices and helps identify diversity issues, but the problem is when this framing begins to creep into how teammates and companies talk and interact with each other. Checkbox diversity results in comments like “You’re in class X, so you must Y” or congratulatory announcements about % diversity statistics without focusing on real inclusivity. (e.g. You might have a black or Latino Engineer on your team, but do they feel like a part of the team and valued beyond just being a black / Latino Engineer that helps your diversity stats?)

Here are some ways in which checkbox diversity has negative, unintended consequences:

• It fails to capture intersectionality of our teammates - I was surprised and excited to discover the variety in survey responses to “What under-represented group(s) do you view yourself as a part of?”. Rather than just mentioning gender or race (a checkbox approach), respondents often self-identified with multiple categories that encompassed race, gender, sexual-orientation, physical differences, religion or cultural upbringing, e.g. “LGBTQ, woman of color”, or “Women; Foreign(ish) people.”. Some called out specific cultural identities like “Black/African-Caribbean”. A checkbox diversity approach encourages us put people in boxes, and doesn’t actually encompass how people view themselves: a combination of experiences that might not always be apparent.
• It fails to capture non-visible types of diversity - Too often we consider diverse teams with respect to what’s visible, primarily gender and race. I don’t want to undercut the desire to build diversity with respect to these categories, but by focusing only on these visible types of diversity, we don’t acknowledge the types of diversity that may not be apparent at first glance: sexual and gender orientation, religion, political affiliation, family status and more. Some respondents said that while they identified with a specific visible class, they feel even more personal identification with a non-visible aspect of their personality (e.g. religion). And individuals might feel persecution in the workplace because non-physical differences often go unacknowledged or subject them to offensive comments.
• It masks sub-diversity issues - Several respondents in our survey identified as a “Asian executive”, “woman engineer in developer products” or “woman in VC”, which point to sub-areas of technology with less diversity. While 25% of all computing jobs are held by women, the VC world is approximately 7-8% female. And while there are many Asians in tech organizations, there isn’t equal Asian representation in the C-Suite. The challenge with checkbox diversity is that there are sometimes subtler types of discrimination at play that don’t get surfaced with broad roll-up statistics.
• It causes over attribution to diversity - When teams are so focused on checkbox diversity, teammates begin to justify opportunities with regards to that person’s diversity qualifications instead of their individual qualifications. The teammate with the opportunity can feel tokenized or unqualified, and other teammates might feel resentment, none of which are a desirable outcomes.
• It causes underrepresented teammates to feel increasingly alone or tokenized - A couple of respondents pointed out a trend I have felt, but never really articulated: when leaders or teammates start to talk about our roll-up statistics, it can come across as not acknowledging that there are real people behind these stats. Respondent's comments reminded me of an experience I had in 2012, when Google’s head of HR said that >25% of Google’s tech force was women. As the only woman on a 10 person team, I was at first suspicious of the stat and then angry. I was dealing with a very unbalanced team and had a lack of female role models, while leadership thought we doing better than average. A lot has changed since 2012, including Google sharing more specific and less optimistic diversity data publicly, but this kind of percent-based rhetoric is still used very frequently throughout Silicon Valley and it can feel marginalizing to the people being described in the percentage. I wanted to share this parallel experience so I can tell the story while protecting the anonymity of respondents who still feel this way in 2017.

An alternative to checkbox diversity is advocating for a diversity of perspective: getting to know a teammate or candidate with respect to all of the different perspectives they might bring to the table, and actively hire for people who represent a different perspective than those already present on the team.

Some ideas for bringing a diversity of perspective into your organization:

• Actively recruit teammates with different perspectives - Assess your current team across the perspectives it already has (It’s okay to think about checkbox categories here, as long as you don’t think of an individual as possessing only one perspective. Think about the intersectionality of your teammates). Then think about what’s missing or unbalanced. Actively recruit people to your team with different backgrounds, skills, or experience than those already on the team. E.g. Say your technical team came together because you were all on the same co-ed Ultimate Frisbee in college, and is equally split across genders. As you expand your team, you might want to recruit someone from a different age group, isn’t interested in frisbee, and came from a different educational background than your alma mater. (Also, see these tips for diversity hiring.)

• Give your team a forum for expressing identity - You’ll never know how many perspectives are currently on your team if teammates don’t talk about who they are outside of work. Here are some ideas:

  • Team introductions - When a new person joins your team, have an intro email that allows them to describe their professional experience and who they are outside of work. Bonus: Have everyone include their preferred pronoun (e.g. “Preferred pronoun: she”) to make gender identity easy to navigate.

  • Have regular team lunches - Make sure everyone on the team attends, and ask people about their weekend plans.

  • For bigger teams:

    • Host listening lunches - As a team lead, you can organize lunches for different groups (e.g. Women’s group or LGBTQ group) for them to talk about their experience in the workplace. Just listen. You’ll learn a ton.  

    • Encourage Show&Tell - At team offsites, host a Show&Tell as a palette cleanser session. Encourage people to teach their other teammates about a skill or talent they have outside of work.

• Proactively solicit different perspectives during meetings - If you’re having a meeting and a teammate might offer a counterpoint to the discussion based on their experience, actively solicit their feedback (e.g. “Wei - You regularly volunteer at a women’s shelter. Do you think we’re missing any privacy issues with this feature?”). By actively soliciting this difference of perspective, you can make better decisions by considering more options while simultaneously reinforcing to your team that diversity is valued on your team.

In conclusion, checkbox diversity still has it’s place in holding organizations accountable for diversity in the workplace, but its role needs to stop there. We need to start talking to our teams and potential teammates about who they are across all the many identities they may hold.

Observations from Maker Faire Bay Area 2016

This weekend I had the opportunity to run a booth at the Bay Area Maker Faire: Microcontrollers for Hacking LEDs. My goal was to have folks writing a program in a minute or less, and we got at least 100 people to write their first program this weekend! It was exciting, rewarding, and taught us a lot about how to encourage diversity in tech.

If you visited our booth at Maker Faire and are looking to reuse our booth setup for your own educational purposes, I’ve put all our resources on on Maker Faire 2016 Project page.

My Maker team and I huddled after the event, and here are some of our main take aways (context here is that our booth had folks coding the animation for a nightlight):

1. Yes, anyone can code! And anyone can get joy from the power of coding! - From the 5-year-old who exclaimed “I want to do it again!”, to the skater teenager who looked too-cool-for-school and then clapped with giddy joy, to the grandma who spent 20 minutes writing new programs for her nightlight, our booth proved that anyone can code. Not one person who gave it a try walked away without having their program run. And for those of us in the software industry, we can often forget what it feels like to see your first program run. The smiles, the spontaneous laughter followed by “I did that?!”, and the feeling of empowerment were all things we were so happy to give this weekend.

2. The narrative of “I can code” is missing - While we got most folks to walk up to our booth, the ones we missed were the ones who said “Oh, I don’t code” and walked away. But if multiple 5-year-olds can do it, what’s the say your average adult at the Maker Faire can’t? It’s just that folks have identified themselves as a non-coder, and as a result, they’re missing out. Our favorite visits from this weekend were the adults who said “I can’t code”, but they gave it a shot anyways. They always left with the biggest grins.

3. The language of coding isn’t inclusive, but it can be - We A/B tested a number of different invitations over the course of the weekend. We tried:

• Come code with us!

• Would you like to customize this nightlight?

• Would you like to program this nightlight?

• Come play with this nightlight!

Probably not shocking: “program” and “code” performed the worst. “Customize” and “play” did far better in encouraging people to approach our demo. “Program” and “code” probably tap into the “I’m not a coder” narrative that’s been baked into people’s sense of identity. But everyone thinks that they can “customize” or “play” with something. For those in the coding education space, we encourage you to experiment with the language when you introduce coding. We found that moving the language to a more inclusive framing around play and customization encouraged more people to give it a shot.

On the flip side, we also saw a few folks be unnecessarily dismissive of their own children’s coding. We would conclude sessions with “You just wrote a program!”, which a couple of parents followed up with “barely” or “but she only changed the color names.” These kids were deflated when their parents made these comments. But there’s no reason we really need reserve labels because “real coding is X”. We can all be coders; we just need to start from a point of inclusiveness.

4. We have an opportunity to inspire girls when they’re young - We saw a distressing trend this weekend: We saw plenty of girls before age <15 who were willing to give coding a shot, but few young women from about 15-25 invited themselves to code. Many women with boyfriends or husbands pushed their partner forward and let them interact with the keyboard, or hung back altogether. The documentary Code: Debugging the Gender Gap does a great job of explaining how women at this age tend to drop out of science. Nothing we were able to say to these women got them to approach the keyboard. Our main take away: help girls before age 15 see themselves as coders. We tried to do this by ending interactions with the <15 crowd with “you’re a coder now” or encouraging natural talent if we saw it.

5. There are lots of amazing people out there who are working on tech diversity - One of the amazing things about Maker Faire is the number of inspiring folks working to build beautiful things and educate. I had the pleasure of meeting lots of educators and makers this weekend. Specifically, I wanted to tip my hat to the Blind Arduino Project. They’re helping folks with disabilities connect with the Maker movement and technology. Find more pointers to coding education and diversity in tech resources on my Resources page.

Thanks to the team that made Microcontrollers for Hacking LEDs happen! 

Pictured left to right: Mom, Tyler, self, and Amanda.

10 tips for hiring managers to increase diversity

The following 10 tips are tailored to any hiring manager in the technology space looking to increase diversity on their team.

1. Ask for diversity targeted referrals - When sourcing referrals from your own team, explicitly ask for diversity referrals. Most people tend to know folks like themselves (gender / race), and their first thought for referrals might be within their own group. To improve the amount of diversity in your pipeline, explicitly ask for diversity referrals to get folks thinking beyond their immediate circle. To get really hands on, consider sitting down with each team member and walking through their LinkedIn network with an eye towards diversity.

2. Write inclusive job descriptions (esp. for gender diversity) - A body of research shows that how you write your job description makes a difference before a candidate even reaches out. Consider reducing the number of required qualifications. Men are more likely to round up on their accomplishments, whereas women tend to round down and opt out of applying to jobs where they don’t meet the minimum requirements even though both the man and woman in a given scenario might be equally qualified (HBR article). Also take a pass to ensure the adjectives and phrasing could be attractive to women (examples and study) and that there aren’t implicit or explicit mentions of gender or race in the job posting. 

   1. Resource: Textio will test your current job descriptions for gender inclusiveness.

   2. How to measure job posting appeal to diversity candidates? Look at the gender ratio of applicants. How does it compare to your industry’s gender ratio? Aim for higher than average, and if it’s not there, tweak your job descriptions or maybe even A/B test to measure the impact. Continuous experimentation is key.

3. Interview at least one diverse candidate for each role - Apply the Rooney Rule (or take it even further like Clara Shih), where you interview at least one qualified diverse candidate before committing to hiring for a role. When I’ve pitched this to other hiring managers, this suggestion receives the most skepticism. They say it’s hard to apply the Rooney Rule since most hires are opportunistic and the pipeline doesn’t often produce diverse candidates. Ask yourself, though - is the trade off worth it? You might fill a role on your team one or two months earlier, but you’ll lose out on the opportunity to have more diversity on your team for the next few years.

4. Run a re-engagement campaign - There are two flavors of re-engagement that can increase your diversity pipeline:

   1. Reaching out to rejected diversity candidates - If you’ve borderline rejected diversity candidates, consider reaching out again. Six months to a year of extra experience might be enough to give them the skills they need to pass your hiring bar. These candidates might not proactively re-apply, but could be some of your most qualified candidates.

   2. Reaching out to Boomerang hires - Boomerang hires are successful hires who have left your team or the workforce, especially mothers who might have left your team to start a family. You already know these candidates are qualified with a track record of success, and maybe all they need is a little extra nudging to come back and work with your team.

5. Require at least one diversity interviewer - Requiring at least one diversity interviewer for a diversity candidate has benefits for you and for the candidate. For your team, it ensures that diversity hires aren’t inadvertently rejected due to the unconscious bias of a homogenous set of interviewers. For the candidate, it demonstrates that minorities are included in your decision making process and makes the role you’re hiring for more attractive. As the hiring manager, when you evaluate interviewer feedback, look for differences between the interviewers for indications of unconscious bias (e.g. Male interviewers saying the candidate is “too nice” or “passive” and a female interviewer not noting any personality issues).

6. Make a public commitment to diversity - Making a public declaration to diversity hiring and development signals to prospective hires that you actively care about diversity and that they can expect support once they join your team. This can be another tactic to make your role more attractive than other roles the candidate is considering. If you’re looking for inspiration, here are public diversity support statements from Facebook, Google, and Pinterest. These are larger organizations making this commitment, but consider a one-pager about your commitment that you can share with your immediate team.

7. Foster an inclusive and supportive community - How your teammates talk about your team with candidates helps to sell your role. For diversity candidates (many of whom may not have come from previously supportive environments), showcasing that your team cares about and supports each other makes a difference. One easy tactic would be to use inclusive pronouns when giving examples or talking about users during the interview.

8. Do champion calls to sell candidates - Once you've decided to hire a diversity candidate, give them a champion call from someone senior in the organization to sell the role. This signals that they’ll get visibility within your organization from the beginning. Also consider a diversity champion call, where a more senior member of the same minority group pitches the candidate on joining the team. This also signals that underrepresented minorities can achieve high levels of accomplishment within your organization.

9. Bootstrap advocates from previous teams - Senior teammates from underrepresented minorities can be hard to find or may not exist within your organization, so it might be hard to source your senior champions for sell calls. Champions don’t always need to come from within your immediate org. Enlist former colleagues that know what it’s like to work with you and can vouch for you and your organization. Ask them do some champion calls to diversity candidates on your behalf.  

10. Hire junior folks from underrepresented minorities - The pipeline for diversity in tech is getting better and better each year (thanks to an increasing number of diversity outreach programs), so if you’re struggling to hire more senior diversity hires, turn your attention to hiring junior diversity candidates. Being the first or second underrepresented minority on your team can be hard (i.e. diversity hiring is better when there’s already momentum) and more senior hires might be hesitant to join a team without an existing track record of diversity hiring. However, junior folks might not think about minimum diversity hiring as a strong criteria when choosing a job. And once you have a more diverse team, hiring senior diversity leaders may become easier.