Chief of Staff for a Week

I help solopreneurs and small teams flourish by acting as Chief of Staff for a week.

I worked alongside the founder of a brand new company for three days. We rented a coworking space in Brooklyn and went into war mode.

On the first day, I asked a lot of questions. I built an internal mental model of her, her company, its vision and purpose; the company’s values, goals, active projects, current obstacles, and next actions.

I offered reflections, encouragement, suggestions.

And then we rolled up our sleeves and got to work.

In her case, priority number one was unblocking and reframing some issues she was thinking and feeling through.

Priority number two was building productivity systems and skills. I built the Digital Productivity Coach, which is all well and good by itself, but frankly life-changing with an expert there to take U through the process step-by-step.

In three days, we got to Inbox Zero, built task management systems, and restructured her processes for sustained productivity.

On the last day, I left her with a number of suggestions for going forward — she should talk to this person, hire that person, read this book, etc.

Her company was already a great idea. She’s got that special spark, where U know someone is going to succeed no matter what. And: doing it all by herself would have taken years. That would have been… suboptimal.

I brought everything I knew to the table to help unblock her and unleash her new company’s latent creative energy.

I brought my expertise in productivity and strategy, but also emotional intelligence, psychological awareness—deep, intuitive, hard-earned human know-how.

Years in monasteries, nonprofits; doing fundraising.

Building The Service Guild — neither a company nor a nonprofit, but an “island of misfit toys,” a collection of weirdos doing work together for fun.

Many hours of talking with many many many many different kinds of people in ten, a hundred places and ten, a hundred distinct cultural milieus.

Her company is flourishing now. The clarity and activation energy lasted after I left.

Who is this for?

  • Lonely solopreneurs in need of another perspective on their life’s work
  • ADHD genius-entrepreneurs in need of body doubling
  • Head-in-the-clouds visionaries with big dreams who are stuck on what’s next
  • Teams that are mired in the same old issues and debates

Who is this NOT for?

  • Someone who has a whole team that’s running perfectly and smoothly
  • Someone who is not willing to learn or grow, to try something new and different
  • Someone who thinks emotions and feelings and psychology should stay in the therapist’s office, at home, but never come to work

Format

My job is to understand your company, your vision, your goals and projects. I’ll ask lots and lots of questions about your challenges, listen deeply, and digest what I hear.

I’ll pattern-match based on everything I’ve seen before, and do everything in my power to help U prioritize, unblock U, propose novel and unexpected solutions.

My base will be by your side. Body doubling, emotional support, unblocking what’s stuck — whatever it takes.

There are no guaranteed deliverables. No slide decks from me, and no homework for U.

What U get is me — my presence, my brain, my energy. I’m confident a little bit of Tasshin will be good for your team and your work. And I’d bet anything it’ll be fun for me, for U, and for all parties. I’m already looking forward to it!

Options

There are three variables: how long an engagement U want, for how many hours per day, and whether we work remotely or in-person. We’ll figure out the right combination for U.

  • Duration: A single day to shake things up, a multi-day engagement (2-4 days), or a full week. The full week is where the magic really happens.
  • Intensity: Flexible (6 hours/day — I manage my own time, but I’m working for U) or Full Focus (9 hours/day — U get my complete, exclusive attention).
  • Location: Remote or in-person. Details below.

Remote vs. In-Person

I’m always happy to work remotely in US-based timezones, and can negotiate other timezones. I can also come to U — or U can come to me. Either way, we’ll want to schedule in advance to find a mutually workable time. U deserve me at my best!

What happens after?

This is a one-off, short-term engagement to start. At the end of our time, we can discuss further possibilities.

Outcomes

Every engagement looks different. Yours could involve:

  • An unblocked psychology around work
  • A custom Productivity Overhaul
  • A full-team training on Using SOPs
  • Reflection on team dynamics that help build the workplace culture U dream of
  • Abundant activation energy that lasts for weeks and months

Above all, I hope U will find that things go better with me around.

Testimonials

Hiring Tasshin as a Chief of Staff for three days unlocked more for me than I had been able to accomplish on my own in three months as a solo founder. Tasshin’s presence alone is a huge unlock: over the course of three days, he helped me go from 87,000+ unread emails to Inbox 0, expertly navigated through the cloud of unstructured and abstract “responsibilities” in my head, and turned them into actionable, digestible sets of tasks, projects, and goals I can accomplish. He paired this guidance with implementation, helping me restructure my barely-existing process into a reliable and lightweight system for sustained productivity. Tasshin supported me through parts of the process that were surprisingly emotional with warmth and care, totally without judgement, only a real and earnest desire to help me flourish. I would recommend Tasshin to anyone.

— Tori, Founder, Soup

The conversation got farther than it would have without you, since having a third party, and more suggestion/structure is helpful for that. You are very present and able to hear things and keep all of a conversation in mind such that you can reference and relate the points, and ensure that things don’t get missed. This type of team building / mediation / conversation is something people do professionally and it benefits people in all sorts of corporate or organizational settings.

— Manager, Client Company

Cost

Let’s discuss! I want to hear about what would work for U.

This can be variable based on whether it’s remote or in person, how many days U expect, whether I’m traveling to U, whether I can manage my own time or U want my full attention for 9h a day…

Fill out the intake form and we’ll find a price that feels great for all of us.

If paying for a service like this feels prohibitive, here are some affordable ways to get much of the same benefit:

Ready to work together?

Fill out the intake form.

If we’re a fit, I’ll reach out to schedule a call to discuss what working together might look like.

The art in this post was created by Sílvia Bastos, and is licensed under a CC BY 2.0 license. You can support her work on Patreon.