Leading Geeks

Can they actually be led?

Is this what men feel like at work?

I am ridiculously happy with my job and my company.do I want to be a man?

And, this morning, I realized that – until now – I’ve never worked anywhere that I could just be me. Where I’m treated with respect. Where I don’t have to reassert myself many, many times in order to be treated like a peer, and then have to tell myself many, many times that it’s ok to be considered a bitch and get ahead rather than be considered nice and stay stuck.

My colleagues respect what I say. Seek my opinion. Follow my leadership and simply expect me to follow theirs.

I don’t have to constantly prove myself in ways that men around me don’t. I don’t have to yell at meetings. I don’t have to pretend that I’m someone I’m not. I don’t have to make the choice between a bitch who goes somewhere and a fun person who doesn’t.

And then, this morning, when I was reading about the GitHub engineer who quit, I found myself wondering, “Is how I feel with my current job what men feel like at work?”

Suddenly, it makes more sense to me that men are more easily considered superstars. Because here’s what’s happening to me:

  • When I don’t have to spend my energy fighting, I spend it on ideas and execution instead.
  • When I don’t worry about how my comments come across, I express my thoughts more.
  • When I don’t get disproportionately penalized for being wrong, I take more risk.
  • When I don’t feel held to a different standard, I take care of myself and don’t get sick as often.
  • When I don’t find myself judged by my gender, I can ignore it and make better working relationships.

I realize that men have other challenges at work. I’m sure they’re challenges I can’t even imagine. And I know that no one escapes the repercussions of crappy, political, hostile environments.

But without gender pressure, I can get more done. I can be better at my job. I can be happy at work. My stress level is shockingly low, despite feeling all the stresses of a crazy seed-stage startup and the full measure of our growing pains and limited runway.

Is this what men feel like at work? It’s more powerful than I ever imagined.

How not to sell product (or why I hate Salesforce right now)

salesforce-sucksSo we’re looking for a CRM. Lots of startups are. It happens. You get to the point where you can’t track stuff in spreadsheets, the cheap stuff drives the marketing person (i.e., me) completely nuts, and you have to grow up and pay for something real.

Okay, no problem. so we’ll look at options. Oh, two of us know Salesforce really really well? Cool. Let’s look at that. Do some research. Figure out what kind of deals other companies get. Fill out a web form.  Awesome.

I naively thought that Salesforce would have its crap together with selling. After all, IT’S SALESFORCE. They wrote one of the rulebooks that I’m basing my sales process on.  Also, I thought, since I negotiated hundreds of software contracts during my 11 years in IT, that this should be a pretty easy negotiation.

And then… sigh.

I like sales reps. Even new ones. Except that the one we got had no idea whatsoever how to handle this deal. My coworkers got to the point that they could tell when I got him on the phone, because my body language and voice tone got rather amusingly annoyed.

I don’t know that I realized how badly a sales rep could screw things up with a customer who WANTS TO BUY, but this guy did. I spent the morning looking at other CRMs, and I emailed his boss a few minutes ago to ask for a different rep. I’ve gone from 100% wanting to build my business on Salesforce to just wanting this guy to go away so that I can set up my sales processes without getting stabby. Well, MORE stabby.

What did he do? So glad you asked!

  1. Kept trying to get to the “decision maker”. Key problem: I’m the decision maker, idiot. Yes, my CEO will be pulled in to make sure I’m not smoking crack (or maybe to play bad cop), but you’re an idiot if you’re selling to tiny startups as your job and you can’t figure out that “Head of Growth” might have a bit to do with making the decision.
  2. Followed the script. I said, “I want pro because of the following reasons:” He then walked me through all of the questions that got us right back to the same conclusion. Sigh.
  3. Overuse of the nuclear option. Hint: Saying, “I’m not sure that Salesforce is the right fit for your company” when ALL I ASKED FOR WAS NON-LIST PRICING on every effing call was overuse.
  4. Leaving the breakup voice mail too soon. Yeah; I do have a full time job. Sorry I didn’t get back to you that same business day. Thanks so much for breaking up with me.

Good grief. I can’t believe how hard he tried to lose this sale. Should be interesting to see if his manager can salvage the deal.

Useless Feedback

English: Angry cat

English: Angry cat (Photo credit: Wikipedia)

An email ruined my weekend.

(And I’m still mad.)

It was an email filled with extraordinarily useless feedback, including completely false accusations. The person who sent it was so unaware of her own behavior and self-blindness that I’m still bewildered, puzzled, and confused.

My gut response, of course, was to reply with an email that would set her straight! It would point out that SHE was the problem – not me. That I had no fewer than five examples of other people who had experienced insult at her hands. I wanted to make sure that she never – ever – falsely accused me of things that were HER FAULT again.

A far smarter (and less pissed) person  stopped me before I could send this email. This email that would have been filled with feedback just as vitriolic and useless as the email that ruined my weekend.

I’ve decided (based on the advice of this wise person) to wait until I calm down and to respond later to the false accusations. What I did on Saturday was to ignore the email and re-ask the simple question that I asked in the first place. Why? I have to get this project done! Her response, as insulting, juvenile, and horrifying as it might be, is completely immaterial to the project itself.

And now, as usual, I find myself introspective. I wonder how many times I write my own judgement into email exchanges where it will be completely useless, distracting, and unproductive.

In order to not be as much of a PITA as this woman was this weekend, I’ve decided to ask myself the following questions before shooting my mouth off at someone:

  1. Am I just pissed? Do I simply want to make the other person pay? If so, I need to put down the computer and hit the punching bag instead. My words can be really brutal, and I need to be careful about how I use them. If I’m not pissed and will move forward, I can go on to the rest of these questions.
  2. Am I writing an insult? I might think that the other person is being cold and emotionless in her email, but calling ANYONE that is an insult, no matter what. Maybe I think she’s being overly emotional, but actually telling her that will either exacerbate her emotions or just piss her off.
  3. What result do I need? This question was the brilliant one that my friend asked me this weekend. I WANTED to tell this person where to get off. I NEEDED to push the project forward. The interesting thing is that answering this question was what caused me to fork my actions – get the project done first, and deal with her problematic communication style later (after the holidays and after I calm down).
  4. Is my feedback useful? If she can’t take action on what I’m writing, why am I writing it? If she asked me for an example and all I did was restate what I wanted (without giving an example), I gave her useless feedback. Am I using too many sentences? Is what I need from her clear?
  5. Am I being truthful? Am I accusing her of something that’s actually my own fault? Am I telling her that she’s the troublemaker when I know that I’ve had arguments with three other people on the team similar to the one we’re having now? Am I accusing her of something that’s just untrue? Maybe I’m pissed and I’m trying to pull in something bigger so that she understands her actions better. I’m probably better off not doing that – all I’ll do is offend her and make things worse.
  6. How does she think? At my day job, I work with a couple of guys who are my exact Myers-Briggs type. This means that I can communicate with them in my own language, as it were. I can explain my motivations for doing something, and they’ll have similar motivations – my reasons will just make sense. This is NOT the case with this weekend’s offender. In order to get her to change her communication style such that her emails no longer ruin my weekend, I need to understand her better. I need to understand what kind of motivation SHE needs to change her behavior.
  7. Do I just want to hurt her back? Am I just looking for my pound of flesh? Do I just want to hurt her like she hurt me? Yes, this is the same question as #1, but when I’m mad, I need to stop and think more than once, so I put this in here again.

Eventually, I won’t be angry any more (usually my anger lasts less than an hour – this was a horrifying email!). If I’d sent the vitriol-filled hateful email, I’d eventually feel bad about it. I’d also possibly have damaged a relationship that I want to last a long time. As satisfying as it would have been to rip her a new <expletive deleted>, that would only have been momentary satisfaction. I’m really glad that someone talked me off of that ledge, and I have a feeling I should bookmark this post for the future!

You’re all irresponsible yutzes.

Well, maybe not YOU per se. But the total mushrooms that I’m reading today.

Stupid IV

Stupid IV (Photo credit: LauraLewis23)


For those of you who don’t have an IV drip of social media like I do, here’s what I’m talking about: LinkedIn published its list of top “overused” words. The word “responsible” came out on top.

Shocker, eh?

Here’s where the yutzification comes in: TechCrunch (and other sources) then started talking about how everyone likes to call themselves “responsible” on LinkedIn.

No! Wrong! Yutzes! (Yutzen?)

The reason “responsible” is used 2X as often as other words is because half of LinkedIn starts writing in a position description, “Responsible for…”

As in describing responsibilities. NOT as in calling yourself a responsible human being.

Dear heavens, was that really THAT hard to figure out? Take a moment and engage your brain, people.


Are you killing your managers?


Psycho (Photo credit: dpratstur_IBZ)

It’s easier than you may think to ‘kill’ your managers.

I’m personally not the greatest middle manager in the world, but I’m grateful for my time as one, since it helped me understand just how painful middle management can be. And it made me realize just how easy it is to kill them. To make them feel powerless. To demoralize them.

Just remembering that makes me shudder.

At any rate, here are some things to watch for to see whether you’re going to be the cause of death to your middle managers.

Making them feel boxed in

Once, a VP of mine told me that he just wanted me to do this one thing. That’s all. The problem is that this one thing had a lot of issues:

  • It would take 30+ hours of my week
  • It was mind-numbingly boring for me
  • It would make my team feel like I was stalking them
  • It wouldn’t actually improve my team’s performance (in my opinion)

When I tried to reason with him, he told me I didn’t have a choice. I pointed out that I didn’t have 30 hours in my week and that I had the biggest team. He still said I didn’t have a choice.

Finally, I told him that I’d be looking for another job.

He backed down a bit at that point :).

But seriously, putting your managers in a box so strict they have to threaten to quit? Yeah; that’s killing your managers.

Expecting godlike knowledge

If you’ve created a working environment where you expect your middle managers to be able to explain every single little bit of behavior on their team, you’re going to be wanted for murder soon. Expecting them to be on top of every single thing without ever having to go back and check or run numbers is completely ridiculous. It also creates an environment where very little gets done.

Yup. Very little gets done.

Why? Because folks are so busy running numbers to explain every little thing that they do nothing to actually move the needle. Folks are so busy covering their butts that they don’t innovate. And because your middle managers must effectively become micromanagers in order to meet your standards, and that’s Really Not Cool.

Insisting on perfection

Once, my team made two mistakes in one week. Two. Heck, I’m lucky I don’t make two mistakes a day, but they were more perfect than I am :). These two mistakes didn’t have anything to do with each other, and they were the result of overwork (IT sucks sometimes) and bad judgment calls.

I was called into the Managing Partner’s office so that a couple of people could ‘get to the bottom’ of what caused the mistakes, and implement whatever measures were necessary to make sure they didn’t happen again. (For the lucky ones of you who don’t know law firms, this is effectively being called into the CEO’s office.)

After 30 minutes of tense back-and-forth, I said, “Hey – they know these mistakes were wrong, and I don’t think they’ll happen again. If you can find any sort of pattern for me to address, I’m happy to address it, but these were, frankly, just mistakes.

“If my team makes mistakes, it’s usually due to burnout. Burnout can either be at home or at work. If it’s at home, I’ll give them time to deal with it. If it’s at work, then we’ll ask them to do less. But there are no processes or systems that I can put in place in order to make sure that random mistakes will never happen again. If anything, I can only promise that mistakes WILL happen again.”

That shut them up, but almost killed me. So don’t do that to your managers, okay?

Promising false power

One of my favorite moments was when my VP said, “But it’s your choice. You’re the CEO of your team.”

“But <redacted VP>, if I were truly CEO of my team, I would fire three people. May I go ahead and do that?”

Clearly, the answer was no. And we did use the situation to make some massive changes for the good of the three people involved, but beyond whether I would have fired these people or not, I made the comment because I felt powerless in the face of being promised false power.

Other times, I’ve seen this when budget has been promised (and then the project revoked for no given reason) or when folks have been told to go ahead, only to have the project yanked or the game changed randomly by the boss. Don’t promise power or responsibility that you don’t mean. Just don’t.

So… what did I miss? Any other amazing stories of how you killed your managers or were killed by your bosses?

That is NOT hacking!

Dear world:

Hacker inside

Hacker inside (Photo credit: Wikipedia)

You keep using the words, “hack”, “hacking”, and “hacker” in, frankly, bat-poo crazy ways. And I’ve just about had it.

I went to a “sales hacker” conference last week. Do you know how many code snippets I saw in an entire day of presentations? ONE. There were like 22 different talks, and exactly one had code up.

That would have been okay, except that the other sales “hacks” were, uh, doing sales in non-stupid ways. No tricks, nothing sneaky or clever – just being not dumb as rocks.

Dude, if I knew that so-called hacking was just being not dumb, I would have called myself a hacker YEARS ago.

Okay, so I’m a bit biased.  I graduated from MIT, where hacking is an honored tradition. And I suppose it has to do with not being stupid, but it mostly has to do with being wicked clever and playing great jokes:

The word hack at MIT usually refers to a clever, benign, and “ethical” prank or practical joke, which is both challenging for the perpetrators and amusing to the MIT community (and sometimes even the rest of the world!). Note that this has nothing to do with computer (or phone) hacking (which we call “cracking”).

Well, fine, then. I want things to be clever. Or at least have to do with computer hacking if we want to depart from the MIT definition.

But, no. GrowthHackers.com has a list of “hacks” that have NOTHING TO DO WITH HACKING. I, frankly, call these things DOING MY JOB. And you call yourselves hackers, people? Have you no shame?

I recognize that this battle has already ended. I need to give up my fight. I need to stop getting excited about something called a hack. With this rant, I hereby surrender.

This is the way that hacking ends: Not with a bang, but with a whimper.

Telling Stories – Even in Technology

Recently, I got to have a blast telling a story. We put together a story about our company’s two-year history and posted it to SlideShare. In fact, I had so much fun that I’m going to show it, and then get on with my post:

I hope you flipped through that, because I work with a great bunch of folks who have senses of humor similar to mine (which is pretty darn remarkable when you think about it).

But anyhow, on to my point: storytelling.

When I was working on the storyboard for the slideshare, I tweeted:

And it’s true – I had a blast with the storytelling part of marketing.  So I started mentally composing this post all about storytelling and marketing and yada yada yada.  Then I realized something: storytelling isn’t isolated to marketing. In fact, I may have done more storytelling in technology than I do now.

Think about it for a second. What are you doing when someone asks you what’s going on? Or what happened? Or why the $%^&* exchange server is going on?

You’re telling a story.

You may be telling the story of the heat in the server room that caused the hard drive in the SAN to degrade combined with the SAN being too full to replicate when you swapped the drive. (Not that I’ve ever told that story or anything. Nope, not me.) Maybe you’re telling the story of the bug that flipped all the bits and made your product choke for six hours while you fixed it. Or maybe you’re telling the story of a budget that’s stretched too thin for what you need to do.

Whatever it is, you’re storytelling.

And with all good stories, yours needs to have a beginning, middle, and end. It also needs to have a plot people can follow. Frankly, as geeks, we pretty much suck at this. We give too much detail, or we leave out the beginning or the end. Whatever we do too much of (or not enough of), we lose our audience. Or we fail to consider our audience. Or something like that.

We’re always telling stories. If we’re aware of that, our communication – especially to non-geeks – will likely get infinitely better.

My thirty-five cents on tech and sexism

Chromosome X

Chromosome X (Photo credit: Wikipedia)

If you read any common tech blogs, you’ve noticed a bit of an explosion over sexism. There was the stuff at TechCrunch Disrupt, the brouhaha over the Business Insider CTO, and, while not strictly tech, the New York Times article on gender discrepancy at Hahvahd Business School. A bunch of folks have talked about how we need to sit up and take notice – and they’re right.

I’m not jumping on that bandwagon, though. I’m going to write about my personal experiences and preferences.

For anyone who hasn’t been following me for a while here, a bit about my background: I went to MIT. I used to run legal IT departments. I changed careers and went to HubSpot, and then spent two years at Amazon. Somewhere in there, I got an MBA from Simmons School of Management, the only all-female MBA program (can you say VERY DIFFERENT from everywhere else?). Recently, I started as Head of Growth at RecruitLoop. Experience in all sorts of male-dominated environments? Yeah; I have that.

I have experienced (many) vendors presenting their entire sales pitch to my 2nd in command just because he was a man and I was a woman. I have experienced doubt about my tech chops at every turn. I have experienced being “the little girl who spends our money” until I nailed my MIT diploma to the wall. I have experienced being told that I was hired because I was pretty and had curly brown hair. If you name the gender cliche, I’ve probably experienced it.

In all of this experience, I’ve come to some conclusions:

  • I would rather deal with juvenile, overt sexism than subtle dismissiveness. 
  • I would rather work with a bunch of idiots who I can call on their bullsh*t than work with a subtly higher bar than my male colleagues have.
  • I would rather personally start the “that’s what she said” jokes than be judged by every little thing I do.

In other words, in the “brogrammer” culture, I can call people on their crap. In the subtly sexist culture, what exactly do I have the ability to call out? In the “brogrammer” culture, I can just be the chick who will kick the crap out of you if you’re an ass. In the quietly sexist culture, I have become the whiner no matter how I approach it. Someday, the brogrammers will grow up a bit. The quiet ones, however? I’ve never seen any of them change. And working in a quietly sexist culture has been one of the most demoralizing experiences of my career.

I realize not all women have these preferences. I realize not all women are hard to overtly offend. I realize not all women can easily say, “Dude, did you REALLY just go there?”  I realize not all women will do shots, play flip-cup, and drink scotch. And that’s okay.

As I said at the beginning of the post, this is just my preference. My personal aim is to help my company achieve an inclusive balance, which includes me and anyone else who would be an asset to the team. I’ve read enough studies on gender diversity to know that this must include women. So, as others have already said, we (as an industry/culture/world) need to figure this out.

Valuing employees

When RecruitLoop and I were in our final stages of negotiating, we started talking about value. About how my primary concern was feeling valued by a company. Talking about value on both sides honestly is probably what got us to the point where we had an agreeable situation for both sides – we knew where we stood, and both sides could see that we considered each other valuable.

The day we got to a verbal agreement, something surprising happened. They asked for my home address (something about lawyers needing it for the docs), and then, a bit later, sent me an email that said:

Ben at the front desk should have something for you (and your husband) tonight  :)

Just to set the stage, it had been a crazy day. It was my husband’s birthday, I had a flat tire that I had to replace, I was talking to someone I knew from high school about working at Amazon, and I had just verbally accepted a job offer. When I got the email, I was sitting at my desk playing stupid computer games in order to take a much-needed mental break. I usually wasn’t home that early, but (thanks to the car) I was this time.  I looked at my computer in confusion a few times, grabbed my keys, and headed down to the front desk of my apartment building.

As I approached the front desk, Ben (our fantastic concierge) pulled out a wine bag and said, “It’s not from me.”

I may or may not have thanked him. I was shocked. Stunned. I looked in the bag and realized that there was a bottle of Oregon Pinot Noir in it. This meant that they had actually listened to some of our social conversation when I mentioned that wine was one of my hobbies, and that Oregon Pinots were my favorite.  And then they had done something that seemed magical – they managed to get a bottle sent to me the very day that I verbally accepted their offer.

To put it mildly, I felt pretty darn valued at that point :).

What they don’t know, however (until now, of course), is that this gesture was beyond perfect for me…

At one of my law firms, the management team would constantly talk about what employees wanted. We wanted to figure this out, since it would help with morale and retention. Could we ask the partners to give out bonuses, or would more salary help, or whatnot. During these conversations, I’d always say this:

It would mean more to me if the partners gave me a bottle of wine than a bonus. In giving me a bottle of wine, they’d show that they knew what I valued and demonstrated that they value me in return.

Interestingly, I never got a bottle of wine from the partners. But I got a bottle of wine – my favorite kind, no less – from RecruitLoop. Demonstrate that they value me? Nailed it.

There’s a big lesson in this for me. It’s that it’s really not that costly to truly show employees that you value them. It takes attention and a little bit of time, but it’s not that hard.  And while it may not be hard, showing value goes a really long way.

My new job.

winding road

winding road (Photo credit: infraredhorsebite)

“I’m looking for a company that I can live and breathe.”

That’s what I was thinking when I started looking around for a job. As you know, I want to fall in love with my company, and I had sadly fallen out of love with it. Working all hours was feeling like, well, work rather than like something I was excited to do with my Saturday morning. I was tired of seeing exhausted, burned-out coworkers, and I was especially tired of seeing the same thing in the mirror every morning.

I considered staying in Seattle, but I wanted to get back into startups. Or at least take the next step in my career so that I could eventually get my dream job: a role with an early-stage startup that could really turn into something big. I honestly thought that would probably be in operations (11 years IT + >4 years marketing + a lot of people management + MBA = uh, operations?). So I started looking for operational roles, hoping to get enough experience to get hired in ops at a small startup someday, and I started looking in the Bay Area, since there was a HUGE concentration of cool jobs and companies there.

I concentrated a lot on LinkedIn for my job search. It was the first social network I joined back in 2004, and there were a lot of great postings there. I searched for stuff in the Bay Area, and applied to a few roles. At one point, LinkedIn showed me a posting for a Head of Growth role. Okay, so I wasn’t really looking for marketing – I didn’t even have a resume prepped for pure marketing – but I clicked through to the job description.

Something about that job description excited me. Near the end, it asked for HubSpot skills, and I just had to click to apply. I was between meetings, so all I sent was my LinkedIn profile – no cover letter, no CV.

They got back to me right away, and the dance began. It was a series of Skype calls, Google hangouts, coordinating odd time zones, a special project, and a breakfast meeting (when I was down to interview at a different company). And then it was a matter of negotiating. And negotiating some more. And negotiating a little with my husband :).

And at the end of the day, I found my company. The one I can live and breathe. The one that I am so passionate about that, after working there one week while trying to find apartments, I was literally pining away for it upon having to come back to finish my last month at Amazon. And not only did I find my company, but I found my dream job as well – Head of Growth is exactly that role in an early-stage disruptive startup that I didn’t think I’d be lucky enough to find yet.

Hourly RecruitmentI’m excited to say that I’m joining RecruitLoop as Head of Growth.

I could tell you what they do, but then you wouldn’t go to the website, and I think they’re cool enough to visit :). Let’s just say that after interviewing probably hundreds of candidates in my career and working with the annoyances of crappy recruiters and “bounty hunter” types who just throw people at you, I think that what RecruitLoop does is brilliant.

Here’s why I’m so excited:

  • It’s a disruptive company. After having so much fun with disrupting things at HubSpot, I wanted to do it again.
  • RecruitLoop has a mission I truly, viscerally believe in. I have felt the pain that they address.
  • An exciting job – I love growing things!  Companies, people… anything but plants.
  • A group of cofounders with whom I felt an immediate connection. This was vital, since we’ll be working very closely together.

All in all, it’s a company that I can truly live and breathe. Words cannot adequately express my excitement.


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