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Levena Bailey Made My Day

April 5, 2012

One of our newest members at Wisegate is Levena Bailey. She is the senior director of enterprise security at Hilton Worldwide (you know, that little hotel company).

Levena has the honor of being the person in the info security industry that the most Wisegate members had told me I HAD to meet, and who we HAD to get as a member. Well, after several members had told her about Wisegate, I recently got a chance to visit with her (along with Bill Burns of Netflix and Denny Dean of a big insurance company who doesn’t like their name mentioned publicly.)

After spending a little time telling her about who we are and what we are up to (and showing her the site) she wrapped up our call by saying to me (I paraphrase), “I want to thank you for what you are doing. I don’t often hear someone who is so passionate about what they are doing. And, we really need this in our industry. So, thank you.”

Not an exact quote, but that is the gist of it.

I told my husband. I told the team. I told our board. I had a glass or two of wine to bask in the afterglow (haha!).

Never in my entire career have I been thanked for what I am doing. Not once. I understand; I started on Wall Street doing M&A, which doesn’t conjure up a lot of warm and fuzzy sentiments. And in my last two start-ups, I was a vendor hawking a software product. Not that there is anything wrong with that.

Today, I am so glad to be building Wisegate – because I do believe in it and that makes it fun to get up and go to work each day.

Levena Bailey made my day.

Scott Chiavetta Made My Day

April 4, 2012

One of the founding members of our Infrastructure & Operations (I&O) community is Scott Chiavetta, CIO of Alliance Laundry Systems.

I was talking with Scott last week and asked him if we could quote him in a press release announcing this newest Wisegate community. What he said made my (and the whole Wisegate team’s) day. Here it is:

“I strongly believe in the value of Wisegate – the high level of member participation and proactive, entrepreneurial nature of the Wisegate staff set it apart from the alternatives I have seen. I have heard many sales pitches over the years for IT collaboration communities, but Wisegate is the only one I have accepted.”

Then he told a peer or ten about Wisegate, explaining it like this:

“The site allows for collaboration via product reviews, polls, discussion questions, etc. You can host a conference call to get peer views on any IT subject (we are diving into cloud-based CRM; I hosted a call on that and got some useful feedback). The grunt work of setting up events is done by the Wisegate staff, so it is fairly pain-free.”

Wow. That can keep me going for days. Next time I talk to Scott I am going to find out more about how what we are doing that helps him. I really want to know.

In the meantime, Scott Chiavetta made my day.

Wisegate is Like a Search Engine of my Peers’ Brains

March 26, 2012

Recently, one of our members said to me, “Hey Sara, it has occurred to me that Wisegate is like a search engine of my peers’ brains.” I thought this was such a cool way to think about Wisegate.

Which got me to thinking…

Do you remember life before Google? Before we knew about Google and had used it, it was hard to imagine what it could do for us. It was hard to envision how habit-forming it would become; that we would be using it every day. Can you remember that point in time?

That point is where we are with Wisegate; building a service that can help, a service that can change the way we work, a service on which people will come to rely.  We are here to bring people together who have the same job in the same industry and who are struggling with the same challenges — the people you need to know whether you know them today or not, available to share expertise and solve problems.

And we are working to help our members understand how to get in the Wisegate habit.

Yesterday, an immigration attorney was telling me they need a Wisegate because so many in their profession are solo practitioners and if they could come together to share experiences, collaborate and solve problems, it would be of enormous value to the attorneys and their clients.  A few days ago, a venture capitalist was telling me he needs a Wisegate for his founders because great things happen when they get together, but that only occurs once a year. And a few weeks ago, two Wisegate members were telling a group of CISO peers at an annual dinner that the way to keep that meeting of the minds going (between now and next year’s dinner) is to bring them on Wisegate (and here they come!).

I believe in what we are building and that it will become a beneficial habit for our members. And I’d love to hear about how your Wisegate habit has helped you — and how it became something you rely on.



I Really Got Asked This Question

March 12, 2012

I get asked a lot of questions about being a woman CEO, a woman in high tech, a woman executive. For years, this rankled me.  Yes, I am a CEO, and yes I am a woman. I founded this great company based on an idea I had and that I believe in. But I never spent one minute thinking about myself as a female CEO – just a CEO; just Sara, and yes, female (high heels, long hair and lipstick definitely in tow. I’m all girl).

Yet again recently, a journalist asked me the following question:

Do you feel pressure to conform in order to fit in with the guys, or is this outdated thinking? What have your experiences in the (high-tech) industry been like? Is it an industry that’s welcoming of women?

To which I responded:

Every time a woman in high tech (or any industry) conforms to “fit in with the guys,” the only thing that happens is the loss of a good woman. Everyone loses: the woman, if by conforming she is not true to herself; and the company, which won’t have the advantage of that woman’s unique gifts and perspective.

I am strongly against conforming. I believe each person has genius to offer the world (and their jobs) and only by developing and embracing who we are will we ever truly shine and offer the world what we have to offer.

The danger of conforming, and I do believe it is a danger, is two-fold. First, each day of our lives that we are focused on conforming, we are robbed of part of our energy. To sustain a façade of being someone we’re not, we have to think about it, weigh it, act it — constantly. It takes energy to repress who we are. If I am spending my time and energy conforming, I am robbing myself and my company of what I truly have to offer in terms of innovation, ideas, human spark.

Second, conforming is not sustainable. Sooner or later something in us will rebel, will demand that we let our true selves out. This can take the form of burnout, depression, major stress – or worst of all, regret. Will we look back on our lives and be thrilled by years spent conforming?

I certainly have felt this pressure, so I understand the question.

The tech world is a great place for women — for everyone — to bring their unique strengths and talents to the table.

What about you? Have you felt the pressure to conform in order to fit in and succeed in the high-tech world? How did you stay true to yourself?

The Joy of Quiet

February 9, 2012

Ah, the joy of quiet.

This article resonated with me. Thanks to my friend Rich for sending (fascinatingly enough, he gets me.) This month I celebrate 10 years of not owning a television. I have happily missed the “Reality TV” craze, though even without a TV I have certainly heard about it.

I have removed most media from my life, including newspapers, radio and magazines. (The quarterly exception is my on-again off-again love affair with InStyle magazine. It is a pure indulgence I periodically enjoy.) This has been a gradual process and one that, in my profession and my world, makes me odd.

Once in a while, as in this case, someone I trust and who knows me sends me something from the popular press that I will read. I trust Rich, he knows me and so I read it. Without meaning to, he paid me a compliment when he told me I was the first person he thought of when he read article.

I started taking silent retreats in 2007. The first time, I didn’t even know what a silent retreat meant; I just felt drawn to it. I remember flying home from some conference where I was on stage in front of more than a thousand people. Doing that, I felt no fear. The anonymity and passing glory of being in front of a big crowd and giving a talk were all I needed. But as I headed from that experience to spend two nights and one day by myself in silence, I felt terrified.

Though still angst-inducing, silent retreats are now part of my rhythm.

So, I relate to this article. I hope you like it.

And in the midst of our crazy work-obsessed world, I am trying with Wisegate to give our members a bit of quiet. A place where they can hear themselves think, listen and gain insight from people just like them. I’ll tell you more about how we do that in an upcoming post.


The Power of Not Knowing

February 2, 2012

Recently, I wrote about the importance of not knowing and how it opens us up to new learning, even (and perhaps especially) in areas that we think we know well.

Just because you’re an expert and do indeed know an area quite well doesn’t mean you’ve got nothing new to learn. For example, Wisegate members are some of the top experts in the IT field. One of the services we provide these senior leaders is a professional match-making service in which we bring members together who have similar jobs, similar roles, similar challenges and by virtue of this can help each other. We get these members together on calls to talk about a specific topic with which they are wrestling. Recently, we had a group of senior privacy officers talking about the challenges of navigating the ever-changing labyrinth of privacy requirements.

During the call, a member posed questions to the group, then each member in turn would offer an answer or pass. At the end of the call, that first member said to me, “That was incredibly helpful. Those little pragmatic tips are valuable; I can’t get those anywhere else.”

But then added (tongue firmly planted in cheek), “Except for that one person who has it all figured out.” We did have one member on the call who felt he knew it all — and said so. Nothing left to learn, nothing left to ponder.

I would be willing to bet he didn’t learn much from that call. Not because there was nothing left for him to learn, but because he spent the time with an attitude of “I already know.” I have since heard from other members who were on that same call — all senior IT people with lots of experience in this specific area — that in the sharing and in the asking, they got help. And now they know more.

In our society, it is not easy to not know. We are rewarded and recognized from a very young age for knowing, having the right answer, appearing to have it all together. Funny thing is, that very appearance often discourages others from offering insights that might be enormously helpful to us. So by not being open about the fact that we don’t know (because no one knows everything), we end up knowing less than we could have.

Try not knowing for one conversation this week. See what happens. I’ll try it too.



There’s Only One of Me

January 31, 2012

No, this isn’t about feeling stretched thin. I don’t, actually.

This is about the elimination of personas until there is only one of me alive in the world. And how liberating this is.

Existential? No doubt. I’ll go there anyway.

Persona defined:

  1. An assumed identity or character;
  2. The mechanism that conceals a person’s true thoughts and feelings, especially in his adaptation to the outside world (as in an assumed identity or character).

I find it interesting the number of people who read my blog and then say to me something along the line of, “You are really good at taking what you believe and applying it in an appropriate way to Wisegate.”

I hear them say, “You have been able to create an acceptable work persona.”

I have a friend named Joel who is a CEO of a publishing company. He talked to me recently about donning a persona at a conference so he could work the room, schmooz, do the deal. I got exhausted just thinking about it; I remember doing just that – donning the persona that the situation called for. The thing is, I can’t do it anymore. Or rather, I am not willing to. I’m tired of being that tired. There is only one of me.

But I have wrestled with it as well. Let’s look at this blog as evidence. Early on, I struggled with what to say – what was “appropriate” to say here because this blog is about my job, my company, and the subject of work. How did I relate that to me and my beliefs?

When I launched this blog last year, I had just a couple of entries over three or four months. Why? Because I didn’t know what to write. I didn’t know what to say that was “appropriate” (dang I hate that word!). When I put my blog writing through the filter of appropriate-for-work-persona, I came up with: not much to say.

Then I tried taking a different approach. I started writing what I believed coupled with what I have observed and thought about recently; topics that I considered thought provoking or perhaps even helpful.

It was then that things changed. I started having fun with writing this blog – looking for the story that needed telling. I write this in my downtime and thoroughly enjoy it (right now it is Sunday afternoon and I am hanging out outside with Homer and our dogs).

Once I took the filters off, more people started reading it, more comments were submitted, and more people emailed me after reading something I had written. The most rewarding comments came from my husband; he told me after “Courage is a Habit” that I had inspired him that day to have a conversation he had been dreading. How cool is that?!? And I love when members write to me and say something about reading my blog – that they enjoyed it or were inspired. That’s marvelous.

Now that there is only one of me, I have way more fun and get much more satisfaction from my writing. I believe what I write here. I always appreciate hearing from you.

I hope the one of me works for you.

A Funny Thing Happened on the Way to the Blog

January 26, 2012

I’ve had many times lately where it occurred to me that I needed to heed my own words. Words that I’ve written here in this blog, to be specific.

In December, I was going through a tough time, and I needed to remember that we never regret brave . There were days upon days that I wanted to pull the covers over my head and wait until it all went away. My life, however, is not a bad dream, so go away it will not. And I needed to be brave, go ahead, get up, face the day. Do my best.  Do the thing that requires brave.

Then, something else came up (as will happen while we are breathing) and I needed to remember courage is a habit. Just keep doing the courageous thing – whatever the moment or the situation calls for. Be courageous, face the stuff I would rather not face. Wash, rinse, repeat.

Yesterday I was penning the only way to know and I realized how much I need that counsel right now. Because I don’t yet know all the ways we can serve our members. I don’t yet know how we will get Wisegate to a point where we can serve more people in more professions. I don’t yet know all the ways we can help people in their jobs – though that is what I want because it is what I believe in.  So I need to not know, to stay curious, listening and not knowing – that’s how the answers will come.

So I couldn’t help but wonder whether it is axiomatic that if we observe what we say to others, will we find that there are the words we need to hear?

The Only Way to Know

January 24, 2012

One thing I’ve learned: It is only when I can openly not know that I stand any chance of knowing. Pick the subject – doesn’t matter – and this holds true for me.

I recently got a question about Wisegate from a reporter that went something like this: Don’t you think most people are reluctant to admit they don’t know all the answers?

Well, people do ask each other questions on Wisegate — and share experiences that help solve problems. This is an important part of why we are here. And yes, I can sense in some people a reluctance to admit they don’t have all the answers.

I witness that the people who are willing to ask questions and admit that they don’t know are the ones who gain the most knowledge and wisdom (they might also be having the most fun). One member recently said to me, “Wisegate saves me time and makes me look like a genius!” He is one of our most active askers. Funny – his being willing to not know and to ask questions makes him look like a genius. Hmmm…

This has gotten me to thinking about the power of not knowing. When do we learn the most in our lives?

  • When we are children. Before we have the expectation of having it all together, or having the “right answer.”
  • When we are willing to try something new. By definition when we try something new, we will not be experts. We will be beginners. And we will learn.
  • When we feel curious and simply driven to discover.

But we block ourselves from learning when we think we know the answers. And if we aren’t learning, are we fully living?

I have learned a lot by experimenting and experience and study, and perhaps I have earned the right to say “I know” in a few areas of life. For example, I have been working on my baked ziti recipe for years, probably a decade. So I can now say that I know how to make a mean baked ziti. And yet, surely a new tip or method will come my way that will once again improve my ziti. Same goes for roast chicken. Same goes for seeking God.

It is only when I can admit willingly and openly that I don’t know that I truly open to new knowledge and new possibilities.

Try an experiment with me (I love experiments – with life as my petri dish). Step back from something you think you know well and let yourself not know. Be curious. Consider new angles. Ask questions. See what comes of the experience.

And in one of my next posts, I’ll highlight an example from Wisegate of how knowing can rob you of opportunities.

Working at Wisegate (Part 2)

December 13, 2011

A while back, I talked about working at Wisegate and our  recharge breaks so we can see the bicycles.

Here is what I tell the team and here is how we operate:

  1. Assume the best. Assume the best and you will usually be right. If a colleague is late for a meeting, assume the best (e.g., they had a flat tire, forgot like we all do sometimes or Outlook misfired and put it in another slot on their calendar). When we do this we are usually right, it makes for a better environment AND frees up energy we would spend being pissed off for more creative purposes. Energy is a finite resource.
  2. The enemy is outside. The enemy is the status quo. The enemy is inferior ways of getting information (we’ll leave it at that). The enemy is not a colleague, not another team, not me. We are human, we work together 5 days a week (sometimes more) and so we will have friction. This is not a bad thing (see point #3), so let’s remember we are united against a common enemy and it isn’t us. Behave accordingly.
  3. Progress is made through conflict. What is so great about everything being friendly or smooth all the time? That worries me way more than friction. Friction means things are happening; things are getting kindled. As a leader, I need to embrace that if the strategies I outline make everyone happy, I’m not putting enough on the line — and the strategy or direction is suspect. For the team, expect conflict and realize it is a good sign that new things are being created, problems are being solved. The lack of conflict should make everyone way more nervous than actual conflict.
  4. Most important of all, Serve. If we focus on serving our members, we will always make the right decision. If we serve each other and serve our team, we will make the right decision. Serving can mean doing something extra for a member today (every today). Serving can mean going to bat with your team for something you believe should happen or change. Serving can mean – assume the best.

That’s how we operate. Plus three-day weekends to see the bicycles.


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