2023 Remote
Leadership
Walkshop
Algarve, Portugal
Trail Difficulty: moderate
We experienced breathtaking views across the southern coast of Portugal in a week-long walking trip, with panoramic ocean views and coastline walks. This hike allowed us access to gorgeous remote nature while exploring the rugged cliffs of the Algarve and the cobbled streets of the coastal cities.
Algarve at a glance
85,726 Steps
14 Leaders from Argentina, North Macedonia, the UK and across the US
5 Towns across the Algarve (Lagos, Praia da Luz, Salema, Sagres, Cabo San Vicente)
12 barnacles eaten (yikes)
Portugal Walkshop
A select group of 14 people went offline to recharge while walking and wandering in small groups through the picturesque backdrop of the Algarve. As we explored, we would identify a topic and then swap insights, perspectives and stories. The path we followed took us through various trails exploring coastal towns, seaside cliffs, and beachfront trails of southern Portugal. The trails themselves guided our interactions: as the path narrowed we restricted a discussion to a single pair of walkers who could fit together on the trail. And later, as larger spaces opened up, the path allowed us to regroup, slow down, and take stock of our surroundings.
Our facilitator
Mike Jansen has a lot of experience with the topic of remote leadership. He is a leader of the fully remote software development agency, Test Double. They have been a distributed company from day one, and currently have 100 employees across the US and Canada—all focused on improving the way the world builds software.
His role focuses on optimizing company operations for scale and efficiency, building autonomy and accountability with his employees through intentional communication. Since his start with the organization, he has overseen the increase of over 100% growth in annual revenue from returning clients.
Portugal Focus: Remote Leadership
For many of us, the nature of work has changed over the last 3 years. Many of us are now working in distributed and hybrid teams and some have gone entirely remote. As leaders, we have new challenges to create connection, foster a sense of belonging, and improve communication despite the distances and distributed nature of the teams. During the Walkshop, we will explore the concept of remote leadership and how we can learn from each other as we explore a new terrain and a new way of working. Daily facilitated discussions:
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Saturday, April 29th: 8 Miles | 13 Km
Perhaps the most critical challenge for leaders in a remote company is replacing the sense of connection and personal relationships that forge “around the water cooler” in traditional office culture.
As we build our own sense of connection to each other on the first day on the trail, we will explore the various techniques leaders can use to create a sense of belonging in a company’s culture.
As we hike out in nature with other dedicated leaders away from slack, zoom, email and twitter - we are reminded of a very important life lesson:
Sometimes we need to disconnect in order to build new connections.
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Sunday, April 30th: 8 Miles | 13 Km
Day 2 is all about visibility. As we walk along the coast today, we will have incredible views of the ocean, many other fishing villages and crumbling fortresses.
We will use these views to inspire our creativity around the topic of visibility at work. Namely, we will discuss how leaders can improve transparency - not just of information - but in how decisions are made.
We will explore techniques and tools used to improve the access to information so everyone has the same equitable path to information and to decision makers.
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The third day is a day off from the trail. This “inner hike” day will be a chance to physically recover and dive deeper into the conversation together.
When companies first go remote, there are generally two common pit falls:
Employees feel isolated and cut off
Leaders make poorly informed (or under communicated) decisions
This often stems from a lack of context (leading to misaligned / bad decisions) and a lack of connection (where employees feel isolated and disconnected from the broader mission).
The ways that we used to solve these problems revolved around the regular “in office” rhythms (meeting at the water cooler, running into people to build connections and share context, having lunch together, etc). These tiny but consistent interactions of energy created a sense of belonging.
In fully remote company, this regular daily rhythm is eliminated. And these problems of lack of context and connection aren’t solved with virtual happy hours.
We need new patterns and rituals that create the same amount of cumulative connection and context, but relied on less frequent in-person time. We need a new operational drumbeat.
The Wednesday workshop will dive into this topic and the various models that companies have worked to replace their old ways of working.
Thanks to Jaleh Rezaei for inspiration on the theme: https://twitter.com/jalehr/status/1574738170121363459
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Tuesday, May 2: 11 Mile | 16.5 Km
On day 4, we will be in the most south western town on the Algarve, where we will really feel like we are walking to the ends of the earth - where the land, very distinctly, meets the sea. As as we listen to the waves, we will explore ways that leaders evolve their active listening skills get input from their teams.
How can we listen and learn from our teams when we can’t be in person or read body language? How do we get away from reading too much into slack messages or not listening enough to distributed team members?
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Wednesday, May 3rd: 9 Mile | 14 Km Hike
Some leaders fear there will be a drop in productivity when people work remotely and no longer show up to the office every day. CEO’s like Elon Musk are firing all remote employees and mandating the return to the office as being synonymous with a return to productivity.
On the final hiking day, we will explore how remote leaders drive traction in their teams and make progress toward shared goals.
At a meta level, we will also explore what ideas and insights we will each take back with us when we return back home. What have we learned from the hike that we can use to build traction at home?
Homework: Pre-read Materials before the Remote Leadership Walkshop
Hiking Schedule
Friday, April 28th: Arrive in Portugal
Arrive, unpack, and get accustomed to your surroundings.
You will need to get to Faro (either by plane or train). Once there, a transfer (included in your ticket) will take you to our first hotel in Lagos. After check-in and your in-person welcome briefing, we can enjoy exploring this historic, colourful city, which is renowned for its picturesque beaches, dramatic coastline and buzzing nightlife. With its ancient Moorish city walls, 17th century fort and modern marina complex full of bars and restaurants, it's a fantastic city to kickstart the Walkshop.
Saturday, April 29th: 8 Miles | 13 Km from Lagos to Praia da Luz
After a breakfast, begin our walking by wandering through the old and narrow streets of Lagos, which head down towards the sea. We'll see remains of the ancient walls surrounding the town. Follow the coast to Ponta da Piedade, a group of rock formations with carved out rocky pillars, natural tunnels and hidden caves. From here you can admire the varied hues of the amazing sea cliffs and see how the wind and sea have carved out these many varying shapes. The colors of the cliffs are a sharp contrast to the turquoise sea, and it's one of the most beautiful natural scenes in the Algarve. Arrive in the small town of Luz, originally a fisherman’s village but now a charming town with a 16th century fortress.
Sunday, April 30th: 8 Miles | 13 Km from Salema Village to Praia da Luz
We will be taking a morning shuttle to the village of Salema, a laid back seaside fishing village. As we walk along the coast back to Luz, we will come across many other fishing villages and crumbling fortresses. We’ll see the incredible variety of seabirds en route, and have opportunities to stop in a local café to sample some fresh fish while looking at the fantastic coast.
Monday, May 1: Remote Leadership Workshop
On this day, we’ll take a break from the trail to rest our legs and catch our breath. We’ll spend the day doing group work and dedicated discussion. We will take a 30 minute morning shuttle to Sagres, where we will spend the day exploring the town and the topic of remote leadership.
Distance: None. We’ll in town for an “inner hike” for this day’s workshop.
Workshop: 10:30am - 3:00pm
Tuesday, May 2: 11 Mile | 16.5 Km hike from Salema to Sagres
On our third day of hiking, we shuttle to the trail head in Salema. This is the most south western town on the Algarve, where we will really feel like we are walking to the ends of the earth - where the land, very distinctly, meets the sea. The walk today takes us along the coastline with clifftop trails, secret beaches and lagoons. The trail passes the beaches of Ingrina and Zavial, where it's possible to stop at a beach bar and admire the views, and perhaps have a swim and a lunch of fresh seafood.
Wednesday, May 3rd: 9 Mile | 14 Km Hike from Sagres to Cabo San Vicente
Our final day of hiking will take us from Sagres along the high cliffs towards the lighthouse at Cabo San Vicente, the south-western most point in Europe and the final destination for the Walkshop. En route there will be opportunities to discover hidden beaches between the cliffs, admire constant views over the Atlantic ocean and imagine this area centuries before, when every port had a fortress and from where many ships set sail seeking new continents.
At the end of the trail, we will have time to explore the town and the lighthouse which was built over the remains of a 16th century Franciscan convent in 1846. At the end of the day, we will catch a shuttle back to Sagres.
Our closing dinner will be at 7pm, where we’ll recap our experience and relive all of the wonderful memories made over the past week.
Thursday, May 4th Head home
Time to say our goodbyes to our group and head back to reality. Or optionally, stay for a long weekend to explore the Portuguese coastline on your own. No scheduled activities for the day.
"Because in the end, you won’t remember the time you spent working in the office or mowing your lawn. Climb that goddamn mountain.” — Jack Kerouac
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"Because in the end, you won’t remember the time you spent working in the office or mowing your lawn. Climb that goddamn mountain.” — Jack Kerouac 〰️〰️〰️
Portugal Walkshop Trip Guides and Hikers
Trip Guide: Tonia Pankopf
Tonia is a strategic and financial advisor to entrepreneurs, CEOs, and investors. She’s the founder of Pareto Advisors and an active independent board director having served on multiple public and non-profit boards. As a seasoned public company director and global investment executive in senior roles as a Wall Street equity research analyst, an investment banker, and a hedge fund portfolio manager, Tonia has significant experience identifying, unlocking and creating shareholder value.
Out on the trail, Tonia is an avid long distance hiker having covered the entire Appalachian Trail, sections of the Pacific Crest Trail and Continental Divide Trail and crossing the Pyrenees from coast to coast . She has also completed numerous long distance trails in Italy, Spain, France, Portugal, the UK, Patagonia and Peru.
Trip Guide: Claudia Richman
Claudia Richman is the founder and principal consultant at We Grow Forward, a change management and organizational design firm specializing in helping creative and entrepreneurial organizations gracefully navigate change. Claudia has been leading remote teams since the early aughts in the advertising and technical industries and her current work focuses on helping companies build systems, structures and processes that support company and individual growth.
In her late 20s Claudia decided to fight against her bookish nature by going on an Outward Bound trip. That week hiking and camping in the desert changed her life and sent her on an active path that includes ultramarathons, multi-day cycling trips and hikes in Vietnam, New Zealand, Argentina and many European destinations.
Tanarra Schneider
Leader by Design. Badass by Nature.
Ingrid Alongi
Investor, Tech Entrepreneur and Advisor
Gaston Algaze
Building and leading amazing Latin America delivery and operational remote first teams.
Ken Judy
CEO, Stride Consulting. Build custom software guided by customer needs.
Cedric Hurst
Principal & Lead Software Engineer at Spantree Technology Group
Lucas Ward
CoFounder, President and CTO
Vlad Andrijevikj
Espresso-obsessed. I also dabble with computers.
Renee Hawkins
COO at Tecknuovo | Woman of the Year 2021 Women in Tech Excellence Awards | Founding member of Chief UK
Lindsey (Eilbacher) Thrift
Outcome Oriented Product Leader & Coaching Based People Manager
Corey Haines
Principal Software Engineer
Mark Rickmeier
CEO at TXI, Founder of Walkshop, Founder of Kermit Collective, Forbes Council Chair, Fast Company Executive Board
Frequently Asked Questions
What's included in my ticket purchase?
Stay in quaint, local inns and hotels in the Algarve
Relax in private bedrooms
Gain access to the Global Walkshop community (online portal, slack workspace, etc). The learning and engagement doesn’t stop when you’re off the trail - it’s just that start of your engagement with this community of executives, designers, authors, speakers, and hikers.
Airfare and transport to and from Portugal will be your responsibility.
What will we be eating along the way?
Breakfasts and lunches will be supplied by our hotels and lodges each day. Special dietary needs can be accommodated. Each evening, we will have dinner at a local restaurant (but dinner will be covered by each person individually).
What should I pack for the trip?
Backpack that can get wet and survive
Phone charger and converter
Journal
Good pens
Snacks
Lots of extra socks
Good hiking shoes (plus an extra pair of shoes)
Rain gear and extra clothing. Dressing in layers allows you to adjust to changing weather and activity levels. Two rules: avoid cotton (it keeps moisture close to your skin) and always carry a hat
Spare plastic bags (keep things dry)
Sunscreen and sunglasses
Bug spray
Compass
Band-Aids (in case you get blisters)
First aid kit
Flashlight
Whistle
What will the weather be like?
Typically in late April or early May, the weather is between 55 - 75 Fahrenheit (14 - 17.5 Celsius). Nice coastal breezes keep the weather moderate.
How should I train / prepare for the hike?
The hike in along the coastal route is moderate without much change in elevation. The longest day will be our 3rd day of hiking (the day after our rest day). Everyone should start an exercise routine several months before our trip and start increasing the amount of physical activity they experience in a typical day in anticipation of the experience.