Category Archives: STC

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Alisa Bonsignore headshot

Episode 004: Alisa Bonsignore–Introverted Entrepreneur

Category:Introverted Leadership,introverts,Podcast,STC,Summit

Episode 004: Alisa Bonsignore–Introverted Entrepreneur Show Notes

Alisa Bonsignore headshotIntroduction

Alisa Bonsignore is the principal of Clarifying Complex Ideas, a strategic communications consultancy in the Bay Area with clients around the world. We discuss how and why she transitioned from a corporate job to becoming a solo entrepreneur and the challenges she faces as an introvert in that role. We also chat about overcoming reticence in meetings.

  • Twitter: @ClearWriter
  • Email:

Key concepts

  • Solo entrepreneurship
  • International clients
  • Entry points
  • Turning layoffs into opportunities
  • Soul-sucking meetings
  • Cultivating reliable clients
  • The importance of management encouragement
  • Subtext


Once I come in the door they realize that I have these skills and I can make things very accessible for the reader…people go, “Oh, but I could use that for this project or that project.”

And for me, meetings are particularly draining, because as an introvert, being in meetings is just–it just sucks my soul, especially if it’s not a productive meeting.

I tended to be extremely quiet in meetings for many years… almost to the point of invisibility, but that didn’t mean that I didn’t have ideas.

You’ve got the dominant personalities and they’re sort of fighting it out in a way in the meeting itself. But sometimes, it’s not until later on where you get away from the noise, where it starts to make sense, what people actually meant, like… the subtext of what they’re actually asking for.

Resources or Products Mentioned in this Episode



Ben: Joining us today is Alisa Bonsignore. Alisa runs Clarifying Complex Ideas, a strategic communications consultancy in the Bay Area. Her professional mission is to create clarity and build engagement, giving people the information they need when they need it. Alisa helps companies communicate complicated topics, including policy development and sustainability communications surrounding the UN sustainable development goals (SDG), medical devices and pharmaceuticals/genomics, network security, and healthcare information technology. You can contact Alisa at or on Twitter @clearwriter

Ben: Alisa and I have been friends for several years and first met each other at a Society for Technical Communication Summit Conference in Sacramento, and I believe that was around 2012 or so. Alisa helps administer the Introverted Leadership Slack community and provided her insights for the “Introvert in the Workplace–Becoming an Influencer and Leader,” published in Intercom magazine, May-June 2018. Alisa also contributed an article, Introverted Entrepreneurship–Embracing Your Introvert Skills,” in February of 2017. if you’re attending a conference, so you can often find Alisa and me at events hanging out on the periphery and chatting. We are introverts after all!

Ben: Alisa, many introverts face challenges in their workplace. However, you’re a solo entrepreneur, so your experience maybe a bit different than that of others. What is your workplace like?

Alisa: I work from a home office, which is actually ideal for me. I know a lot of people don’t enjoy the home office environment because they feel like there are too many distractions. There’s the television, there’re other things to do, there’s the kitchen. I know a lot of people have trouble with the kitchen [laughing], but for me it’s actually ideal, because I feel like I get a lot more done because I don’t have the interruptions; I don’t have the people popping into the office needing to chat with me or requesting meetings. Most of my clients are based in Europe–well a lot of them anyway. And with the nine hour time difference that means by my 9:00 AM, most of them are gone for the day, so I do a lot of early conference calls. I get my meetings out of the way and then I have the entire day to be flexible and work at my own pace without interruption, and it’s just perfect for me.

Ben: What kind of work do you do?

Alisa: I’m primarily a writer and an editor. I provide communications consulting to companies, usually large companies (but some startups) around their communications plans, and that can range from anything from their marketing communications to more of their technical communications to a broader content strategy to policies and procedures. There’s a lot of things that that sort of fall into that. Once I come in the door they realize that I have these skills and I can make things very accessible for the reader, and then I’m sort of shuffled around from group to group where people go, “Oh, but I could use that for this project or that project.” But, a lot of what I come in the door for tends to be somewhere between technical communication and marketing. It’s more of your white papers and things like that where you need to explain really difficult technical or clinical concepts to ordinary people in plain language. And that’s usually my entry point. But, then I do a lot of things from there.

Ben: That’s interesting. So how long have you been doing the solo entrepreneur thing and what did you do previous to that?

Alisa: So I was doing it part time, sort of, the nighttime freelance writer for several years. But this full-time version of it started about 12 years ago. right after my son was born. I had been working in-house at that time, at a medical device company. It was right here in town. The commute was great. I loved my boss. I loved my team. Everything was wonderful, and I came back from maternity leave, and three days later they announced that they were shutting the entire office down and moving to Boulder, Colorado. So that pretty much put things into perspective and I said, “Okay. Maybe maybe it’s time to do the freelance thing that I’ve been talking about before.” So, that’s what kicked me out the door. And it does help when you’re starting out that you have 400 people in your building who have now scattered to the wind, because those 400 people carry your name with them to wherever they go. So, that was a really good starting point, actually. It was a bit of a kick in the butt, but it was a–It ended up being very helpful.

Ben: So what happened was you had thought about launching this and then you were…

Alisa: Well, so we had talked for years about if and when we ever had kids. that that would be a really good time to go freelance because of the flexibility and the options there, and I wouldn’t be tied down to an office where it was more difficult, right? So we talked about it, but I was in a really good situation at the time so I had no intention of quitting and moving on, because it was really working well for me, because it was a, as I said, a good group and a good manager, and I was really enjoying the situation that I was in until it wasn’t there anymore.

Ben: It’s always interesting what provides the impetus for change and, at least in my experience from many times, it doesn’t mean that we’re necessarily ready, even though we were certainly thinking about moving in that direction. So, in terms of your previous workplace, right now you’re working from home by yourself, you have a good deal of control (or at least the illusion of control) when you have conversations scheduled and things like that. What was it like for you when you were in a corporate workplace?

Alisa: So I think my corporate experience was a lot like what most communicators find in a corporate experience, which is that, as a communicator, you have several different clients internally. You’re not just typically writing for one product manager, or one engineer, or one whatever. You’ve got a lot of people who are pulling you in a lot of different directions, which means that you have a lot of meetings, and a lot of busy time that you might not necessarily be accomplishing, but you’re sucked into a lot of the time. [laughing] And for me, that’s particularly draining, because as an introvert, being in meetings is just–it just sucks my soul, especially if it’s not a productive meeting. I mean, the meetings that I have now with my clients, especially since most of them are Swedish and German, we get on the phone, we talk about what needs to be talked about. We get on, we get off, we move on with our day. It’s not the lingering, 12 people on a conference call. “Hi, who’s this?” “Who dialed in?” “Oh, well it’s Bob here.” You’re not drifting out into that sort of thing.

Alisa: It’s a much more pointed meeting and a much more relevant meeting than what I used to have, and as is the nature of any cubicle farm, when you’re in house, people just pop by, and they’ve got things they want to talk about, and they may be work related and they may not be work related, but they suck your day. [laughing] I found that I wasn’t really getting as much accomplished as I wanted to at the time, because it was–there was so much brain power going into the meetings and the time going into the meetings, and it wasn’t really giving me the time to just sort of have uninterrupted time to do what I was really supposed to be doing.

Ben: So, it sounds like there’s a bit of a cultural difference with your current meetings over the typical in-house meeting as well.

Alisa: Well, and I think too, maybe it’s just a part of it’s cultural with the–the type of culture in Sweden, Germany, but part of it too, I think is, it’s a lot easier when it’s a one-on-one call. You’re either both there or you’re both not, and when you’re there you’re not sitting around waiting for somebody else to dial in, and it’s not that waste of time with all the useless chitter-chatter for 15 minutes. It’s, we’re both on, okay, here’s what we have to cover. Boom, boom, boom. Now we’re done. Great. Have a great day.

Ben: In terms of your current entrepreneurial position, what do you find challenging as an introvert? I know based on what we’ve talked about here and talked about previously, you are able to at least somewhat structure your day. What do you find to be a challenge as an introvert?

Alisa: So I think that onboarding new clients is always a challenge, because you always have to be selling. You always have to be networking, right? So this is why I’ve done a really good job over the years of cultivating reliable clients that I know that I can go back to again and again, because I don’t want to have to do that relationship building. That’s draining to me, because it’s selling. It’s about selling myself. It’s about proving that I can do what they need to have done. That’s exhausting. It’s like job interviewing every time you do it and certainly I prefer not to do that. [laughing] So over the years I’ve done a really good job of really cultivating good people, and even within a company filtering down the people that I want to work with in that company, even if it’s a good company overall to work with, that doesn’t mean that everybody is good to work with within the company.

Alisa: I’ve definitely worked on tha t so that I’m doing less selling, which is helpful to me psychologically, but also it helps because I’m not having to do all of the administrative chasing. So I’m not having to worry about setting up the vendor as a vendor and all these different companies and I’m not worrying about as much how to–who do I contact if I don’t get paid, I already have my contacts, I already know who to reach and it makes it a lot simpler to work with at that time.

Ben: So do you pretty much do all of the, all of your business responsibilities yourself?

Alisa: Yeah, it’s all me.

Ben: So no virtual assistant or anything like that at all?

Alisa: No, no, just all me.

Ben: Alisa, you had talked about meetings and how meetings can be challenging when they’re in a corporate environment, because when you’ve got everybody catching up with everybody to see however you want is doing, but you also have the issue where you may be in a meeting with many, many people, but there’s only a small portion of it where you’re really active in the meeting. Now, for me that is multitasking time, which may or may not be a good thing. (Especially if somebody addresses something to you and you’ve been busy working on something else for half an hour.) So what else–was there anything else that you found challenging about being in a corporate meeting?

Alisa: Well,  yeah, I mean especially in a lot of my roles I’ve had to deal with people who are a lot more extroverted than I am, and that means that they talk a lot. When there are people in the room who are dominating the conversation, it’s not my style to dominate the conversation. I mean, I’ll speak up when I have something that I really need to say, but I’m also not the kind of person who will typically talk over somebody else to make that happen. So if you’re in a room with sales, if you’re in a room with that manager who’s really just like loud and dominating and aggressive or whatever, it’s very hard for me to butt in and be like, “But wait, I have a thought here.” It’s not really–it’s not really my style.

Alisa: So, I tended to be extremely quiet in meetings for many years to the point where–almost to the point of invisibility, but that didn’t mean that I didn’t have ideas. I would be much more inclined after I’d had some time, we’d all met and after we leave the room, sort of like when somebody insults you, you get the great comeback later. After a meeting I walk away and 12 steps out the door, I’m like, I get it now. I know exactly what we need to do because I’ve had a few seconds to process what everybody has been saying and where everybody’s coming from, and come up with a solution that works for everybody, which might not come to me on the fly in the meeting itself.

Ben: Was this anything that your management ever mentioned to you at all? I had a conversation, which is on another episode of this podcast,  with a friend whose manager actually described her-to her face-in a meeting as being a slow thinker.

Alisa: [laughing] No, nobody ever thought that I was a slow thinker to my knowledge. Nobody ever said it to me anyway, but I definitely think that there was the perception–well, I feel like there’s the perception that writers in general are quieter people. I mean we’re not expected to be keeping pace with sales in terms of our conversation and our–our loudness in our domination, right? We are–we are generally,–most writers that you work with are generally more reticent than others. So I don’t think it was completely unexpected, but in my last in-house job, my boss was like, “No, you know what you’re talking about. Get in there and just barge right in and do it!” She was much more encouraging of that–not that anybody else had been discouraging–but she was much more, “Why are you not saying something?”

Alisa: “Well, because, I’m not–I’m not going to interrupt the vice president of something or other who thinks he’s got this grand plan.” And she’s like, “No. Somebody has to interrupt him. This is nothing. This isn’t smart. What do you say? You really got to get in there and do it! Tell them what you think, and do–do what needs to be done!” And so there was much more push there from her, so she was really good for encouraging me that way as opposed to the-the negative encouragement of others. No, she was–she definitely gave me some positive reinforcement.

Ben: It’s interesting because I tend to be reticent, and not that you would believe that now either! [laughing] I tend to be reticent in meetings or at least I have in the past, but for me to feel like I’m going to interrupt this vice president, even though I know this person is wrong in what they’re doing, feels a little bit about, “Oh, look, the emperor has new clothes!” And I don’t want to be that person who points that thing out. But obviously, I’m thinking it, whether I’m–whether I’m saying it out loud or not. [Alisa laughing] So I definitely empathize with what you’re talking about in terms of being hesitant to interrupt. And even now, even as “glib”  as I can be for an introvert in meetings, there’re so many times it’s like, “Oh, I should have said something about that.” “I need to talk to this person afterwards, because they didn’t come across the way they thought they did,” or, “that really might not work the way you think it’s going to,” and for whatever reason, and I’m definitely not always right, but for whatever reason, those flaws usually jump out when I hear them or especially if I read them.

Ben: So, meeting behavior can definitely be a bit of a challenge?

Alisa: Yes. Yeah, for me, a lot of what goes on in conversation–there’s–you’ve got the dominant personalities and they’re sort of fighting it out in a way in the meeting itself. But sometimes, it’s not until later on where you get away from the noise, where it starts to make sense, what people actually meant, like what was the subtext of what they’re actually asking for. They may be barking about needing X, but really, the reason why they’re barking about that, is because they’re under pressure about Y, and–“Oh, if we can address that, then X becomes less relevant. We don’t have to fight about X.” Right?

Ben: Looking forward to the second part of our conversation.


Alisa has a Twitter bot that is sometimes hysterical.

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Saying, “Yes, and…?” to Leadership Opportunities

Category:Leadchange,Leadership,STC,STC Rochester Tags : 

What If?

“Yes, and…?” is the hallmark of improv comedy. It’s also key to our growth as leaders. What if we said, “Yes, and…?” when approached about taking a leadership role in an organization?

For many of us, our first reaction to leadership requests are, “No, because…,” or perhaps, “There’s no way I can do that!” We live in an increasingly fast-paced culture with many opportunities on which to spend our time. Many of us can be quite guarded when considering external commitments. Sometimes being guarded is warranted because of our current level of obligations; sometimes we just have an automatic “No” response. We know what saying “no” provides us: security, peacefulness, free time, and a comfort zone.

Let’s look at what saying, “Yes, and…?” has done for me and what it may do for you.

My “Yes, and…?” Journey

My “Yes, and…?” journey started about 10 years ago when I agreed to be Program Manager for the Rochester Chapter of the Society for Technical Communication. My role was to obtain speakers for educational events and to help set up venues. It was a reasonably small role, and I believed I could do a good job at it.

The following spring the chapter looked for volunteers to fill their election slate. When they asked me what role I was willing to take, I said anything besides Vice President. (The Vice President role includes co-chairing our regional conference and speaking in front of a large group of people. I was not interested. As an introvert, I absolutely did not feel comfortable in that role.)

When the chapter announced the election slate, I was on the ballot–as a VP candidate! Although I didn’t believe I was suited for nor competent to take that role, I didn’t want the embarrassment of withdrawing from the role or admitting I believed it was beyond me. Providentially, the chapter nominations committee saw leadership skills in me that I did not yet see within myself. I did OK in that role. I was partnered with someone who had filled the role the previous year and I was able to act as an “understudy” and not feel as though the weight of the role was too much.

The following year, the dues structure changed in the organization and most all of the current leadership left the organization. (There were other factors–retirements, moves, etc., that also impacted. their decisions.) There was no one more senior than me. I would be the next president. I became the next chapter president. It was a good year, although we had struggles without former leaders to mentor us. I attended my first Leadership Program at the STC Summit Conference in Dallas, met and engaged with other chapter leaders, and began establishing a peer network that has been invaluable to this day.

The Next Step

After my successful year as STC Rochester president, I decided I wanted to help other chapter leaders who might face the same challenge of having no leadership mentors. I joined the Community Affairs Committee and built an outreach program and team to mentor and assist other chapter and SIG (Special Interest Group) leaders. That team made a positive impact. My “Yes, and…?” was agreeing to serve and bringing my vision for a leadership outreach team to fruition.


Fast forward to today. Next week I’ll be installed as the Vice President of the Society for Technical Communication. The following year I will become President. Unlike local chapter elections where 90% of the time candidates run unopposed, this time I had an opponent (who was also a friend). I campaigned actively for the role. I ran for office because that peer network I had become part of through the Summit Leadership Program and the leaders I had helped support, told me they needed me to run because they believed in me. They believed that I would help lead positive and potentially deep changes to the organization that would address our changing demographics and ensure we’d be a viable and influential organization in the future.

“Yes, and…?” and Me

My leadership journey has stretched me in ways I couldn’t have imagined. I’m now comfortable speaking to large groups of people. I’m able to articulate a vision of where I believe the organization needs to go. I’ve learned to build consensus and enroll others in meaningful initiatives.

I love being able to make a difference! Although I was initially tentative and doubted my ability to be a leader, I was willing. I’ve been stretched. It’s not always been comfortable.

I wouldn’t trade the journey for anything.

“Yes, and…?” and You

Please say, “Yes, and…?” when someone (perhaps me) offers you an opportunity to serve!

Will it take you out of your comfort zone? I certainly hope so. We grow through being stretched. We grow through service to others and I believe there’s no higher calling.

Serve where you’re passionate. Make a difference!


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Ben Woelk–Spring 2018 Speaking and Conference Schedule

Category:EDUCAUSE,Information Security,Introverted Leadership,Leadership,Presentations,STC,Summit

Updated 18 February 2018

It’s going to be a busy few months for speaking engagements for the first half of the year! I hope to see many of you.

Speaking Engagements through June 2018

Topic Date Venue Registration Link Notes
Slack for Technical Writers and Editors 23 Jan STC San Diego and STC Rochester Virtual Workshop NA With Sara Feldman; Recording available.
Slack for Communities 16 Feb STC CAC Leadership Virtual Workshop NA With Sara Feldman
Lessons Learned on an Introvert’s Journey to Leadership 22 Feb STC Atlanta Webinar Sign up on Meetup to receive registration instructions
Lessons Learned on an Introvert’s Journey to Leadership 27 Feb Webinar for Quebec City Private
Digital Self Defense 28 Feb meRIT webinar Register Open Registration
Digital Self Defense 20 March American Society for Quality, Rochester Section 0204 Register
Spectrum 2018 25-27 March Rochester Institute of Technology Register on Eventbrite Co-chair, no formal presentation, 40+ presentations and workshops over 3 days
Digital Self Defense 3 April Rochester, NY Private
It Doesn’t Take Magic: Tricks of the Trade to Create an Effective Security Awareness Program 10 Apr Preconference seminar, Baltimore, MD Register at EDUCAUSE With Tara Schaufler, Princeton University. EDUCAUSE Security Professionals Conference, Separate registration required
Different Boats for Different Folks: Tales of Security Awareness Follies and Successes 11 Apr Panel Discussion, Baltimore, MD Register at EDUCAUSE With Sandy Silk, Harvard University; Christine Bonds, Elon University; Emily Harris, Vassar College, EDUCAUSE Security Professionals Conference
Slack Workshop TBD STC PMC Virtual Workshop TBD With Sara Feldman
Summit Leadership Program 20 May STC Summit Register
Temperament-Based Strategies for Excelling in the Workplace 20 May STC Summit Preconference Workshop Register Additional registration required
The Introvert in the Workplace: Becoming an Influencer and Leader 21 May STC Summit Presentation Register
Yes and…: Improv’ing Your Corporate Communication Skills 21 May STC Summit Workshop Register With Jack Molisani; Additional fee ($20) required; limited to 20 participants per session.
Yes and…: Improv’ing Your Corporate Communication Skills 22 May STC Summit Workshop Register With Jack Molisani; Additional fee ($20) required; limited to 20 participants per session.

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