Nick’s coaching FAQ
I’m kicking off a series of posts on topics that come up frequently for my clients. I thought I’d start with an intro FAQ, answering the questions that most often come up when I have initial conversations with prospective new clients. Future posts will tackle topics like technical communication tips and organizational influence strategies. I hope reading this can help you (and your contacts– please forward this freely!) decide whether my services might be a good fit for you. If you want to know more, the next step is to book a free 30 minute intro chat on my Calendly: calendly.com/nweininger.
Q: What’s your background and why are you doing this?
A: I’ve been in the software industry for 25 years now. For most of that time I was at Google, which I joined after graduate school in 2005. I went from individual contributor to tech lead to line manager to manager-of-managers there, and worked on a variety of different teams in the search and developer infrastructure divisions.
I left Google in early 2020 to see what else was out there. My initial plan was to take a travel sabbatical, but the COVID pandemic had other plans! I started coaching out of a desire to “do my bit” to help software teams working on pandemic-related projects. My first client was a startup founder working on remote health monitoring, and if you’re a member of the Y Combinator founders community, you can find his recommendation for me on their “Bookface” forum.
Since then I’ve spent some time working at a climate tech startup founded by former Google colleagues, doing volunteer teaching, and pursuing my musical interests. But consulting and coaching have been a constant through-line, because I’ve found that 1-1 mentoring and collaborative problem solving is the thing I feel most motivated to do and where I can add the most value. As far back as graduate school, my best teaching conversations were in office hours with students who came in looking for deeper understanding of a tricky homework problem. At Google I always looked forward to my weekly 1-1s with reports who were growing in technical leadership and management roles, and I sought out cross-organizational mentoring opportunities whenever time allowed. Thus, freelance coaching lets me focus on what I do best.
Q: What kinds of folks do you coach, and what challenges do you help them with?
A: My clients have ranged from seed-stage founders building their first small team, up to line managers at more established companies who are navigating team growth and big role transitions, such as from manager to manager-of-managers. In my career I’ve personally led teams with sizes ranging from 2 to 45, and coaching can be fruitful for folks anywhere in that size range or even beyond.
Common topics I’ve covered include:
Implementing effective team work processes and cadences.
Delegating and sharing work to avoid burnout and single points of failure and to help others grow.
Best practices for reliable systems design, deployment, and maintenance.
Maximizing team performance and motivation as teams grow and change.
Dealing with conflicts: between members of a team, between peer teams, between leaders and their management chains, between engineering and product organizations, between CTOs and founders.
Effective recruiting, hiring, and retention practices.
Q: What’s your client engagement model? How do clients book time with you, and on what terms?
A: After our initial 30 minute chat, if we both decide that my coaching services are a good fit for you, I will give you access to my private Calendly links to schedule 60- or 90-minute coaching sessions at your leisure. The goal is to find time that fits your schedule, as much or as little as you need to talk through whatever issues are important to you. I often find that clients start with weekly or biweekly sessions to set context quickly and explore challenges in detail, then drop back to monthly or bimonthly as the solutions we discuss get moving. But whatever frequency works for you and for my calendar is fine; there’s no right or wrong trajectory.
I do have clients sign a standard consulting agreement, but it does not specify minimum or maximum hours. Sessions are billed “a la carte” at a flat hourly rate, currently $300 per hour as of June 2023. I send monthly invoices which can be paid by Paypal/Venmo/Zelle etc or by check; some clients find it easiest to put me in their company’s contractor payroll system, and that works fine too. Sessions are typically held over Google Meet or Zoom, though recently I have had some in-person meetings with clients based in the San Francisco Bay Area.
I ask clients to email as much information as possible about agenda topics in advance of the meeting to make efficient use of our time together, knowing that things come up and sometimes the best agenda is “let’s talk about whatever happened last week”. I’m more than happy to get relevant documents from you to read before meetings, e.g. operating notes, product presentations, design docs, org charts etc.
Q: What should I do next if I think I might want to be your client?
A: Just go ahead and book a 30 minute chat at calendly.com/nweininger. Email intros are great too, but that first (free!) chat is essential to finding out whether there’s a good fit.
Also, read The Manager’s Path by Camille Fournier if you haven’t already. I recommend this to everyone in the software industry, even if you have no intention of becoming a manager. Everything Fournier says resonates completely with my experience. The psychological and logistical issues she discusses, and the best practices she offers for addressing them, are invaluable for understanding how software organizations work and why and what different roles within those organizations entail.
