Bespoke Solutions’ Post

Apologies for the delay in posting! With baby #2 due this week, I've been been the GC on our 3-room house reno over the last month. Without further ado: The Importance of a Well-Rounded Chief of Staff in Mitigating the Pitfalls of the Peter Principle for Startup CEOs As a seasoned change management consultant, I've navigated through the intricacies of organizational dynamics and witnessed firsthand the consequences of the Peter Principle, especially within the realm of startup companies. The Peter Principle states that individuals are generally promoted to positions beyond their competence, ultimately resulting in organizational inefficiencies and failures. Nowhere is this phenomenon more evident than in the realm of startup Founder/CEOs, who often find themselves thrust into the highest echelons of leadership on little notice and told to deliver. On Monday she could be coding with three friends since high school, by Tuesday could get VC capital, and by Wednesday be the CEO of a company valued in the millions of dollars and tasked to ramp-up to profitability over six quarters. Few Founder/CEOs survive this transition because they feel drawn to stay close to their product/team working in the trenches. This is the crux of the Founder/CEO befalling the Peter Principle - they are great coders but choose not to be great at managing coders. So, how can they overcome this pitfall? Enter the Chief of Staff – a critical ally in the arsenal of a young startup CEO to avoid the Peter Principle trappings. Unlike traditional executive roles, the CoS operates as a versatile linchpin, bridging the gap between strategy and execution. The COS does this by standing outside of the standard COO/CTO/CRO hierarchy and instead focusing on giving their CEO the three things they don't have enough of: (1) TIME to think strategically (2) BANDWIDTH to explore options and peek 1/3/5 years down the road and (3) COMMUNICATION STRUCTURE to cascade her decisions down the corporate ladder. How does the CoS do this? By: (1) overseeing day-to-day operations (2) being a trusted advisor and proxy when needed (3) handling ad hoc issues across all departments of the company (4) creating strategic initiatives and navigating complex challenges (5) acting as a sounding board and providing critical feedback/guidance every step of the way (6) streamlining operations, aligning priorities, and driving execution across the organization (7) keeping their finger on the pulse of the company. When looking for a CoS, remember their role is to help you rise above the day to day operations of HR, Legal, Marketing, Ops, Accounting, PR, etc.. As such, your candidate's work experience should reflect that breadth. Make sure to look beyond just MBAs. You're not looking for a master of one or two issues - as MBAs often are - rather, you're looking for a diversified corporate athlete capable of deftly handling anything.

A typical problem with scale-ups is when bureaucracy is disproportionate to the company size. When a company with 300 people has the same structure and processes as the one with 10000, something is wrong. I have seen such examples. The downsides of a corporation are understandable and can be forgiven, but when you see a scale-up trying to adopt the same clumsy procedures, it is surprising. Why could this happen? Some of the reasons are hiring and corporate culture. It is inevitable that a startup changes when founders and the initial team have less influence on hiring decisions. And even if they have a strong influence, it matters not only what vibe they are looking for in the new hires, but also what background each new hire brings on board. Some newcomers might turn out to be professional in their job but they will spread a corporation style all over them. They might suggest process innovations that are inspired by working in established companies with hundreds of people. As a result, a company of 300 people will be spending the same resources as a 10000-employee corporation does (for example, with one-third of the staff supporting the money-making processes instead of directly participating in them). Have you seen something similar? #corporateculture #scaling

Lessons on Scaling through Chaos! After product launches and talent hires, the #1 focus for founder CEOs is scaling quickly, efficiently, and consistently. Last week I went to Index Ventures’ event - Scaling through Chaos - where they walked through their research and deep insights on rapid scaling. With interviews and analysis from over 200 top companies, they shared the top lessons for what it takes to scale well. #1 takeaway for Founder - Get used to hiring and talent taking up 50% of your time That can be surprising for founders, especially if you love spending more time on product or sales. But when you’re scaling quickly, building the right talent engine is the biggest and most important way to use your time. Here’s a behind the scenes on more of the top insights from the event: • When you’re growing at a rapid pace, each wave of hiring mean you're essentially building a new company every year • With those changes comes the need to really codify culture and values. Do this early and update when needed. But, what’s more important than just writing down values is actually living them • Few early employees will stay to the later stages. That’s OK and to be expected • Never run more than two executive searches at the same time. It can be time intensive, onboarding and culture issues might emerge, and you might learn you need a different type of leader after one comes on board. • Often founders look to fix problems by redesigning the org structure. But Org redesign doesn’t fix problems. Focus less energy on org design. Just pick one and focus on finding the best people for their roles • What to look for in talent: mission driven, ‘spikes’ of an exceptional skillset, slope potential of growth Tools / Resources: Index Ventures put together TEAM PLAN, a great resource to help map and plan how your teams should grow at each stage. Link in comments!

Everyone working in Start- and Scale-ups in my Network: I came across this insightful article about common mistakes companies make when hiring their first 100 employees, and I had to share my thoughts. As someone deeply invested in the startup and scale-up ecosystem, I believe we can all learn from the experiences of others. The article by Matt Hoffman highlights three major pitfalls that many startups encounter: 1️⃣ Not developing a people strategy early enough: It’s easy to get caught up in product development and customer acquisition, but having a clear hiring strategy from the start is crucial. 2️⃣ Neglecting company culture from the beginning: Culture isn’t just a buzzword; it’s the backbone of your organization. Every new hire contributes to this culture, so it’s essential to define and nurture it early on. 3️⃣ Focusing too much on individual performance instead of team dynamics: In a small team, every member's contribution matters. Prioritizing how individuals work together can lead to greater success than simply measuring individual achievements. The early days are foundational, and the decisions we make now will impact our teams for years to come.To my fellow founders and leaders in startups and scale-ups: let’s learn from these common mistakes! How have you approached hiring in your own journey? I’d love to hear your thoughts and experiences! #StartupCommunity #HiringMistakes #CompanyCulture #TeamDynamics #Examiz https://lnkd.in/ejGkG4fP

Many Founders struggle with knowing when to hire a Chief of Staff, what to look for, and how to best leverage this critical role. That's why Ryan Monk and I are sharing insights we've gathered from helping over 30 Founders find the right fit. Hear our thoughts below:

A curious milestone for this little company: My first employee starts next week! Or in other words, a few more days until I have to get used to saying "we". After quite a bit of pondering, the company strategy is still pretty much what it was a year ago: Provide services (mainly fractional CTO, consulting and CTO coaching) for short term profits, develop products to scale. The services part has been going quite well, but product development hasn't. I found it quite taxing to work on stuff all by myself, with just a few hours per week. So I'm changing my approach: Firstly by collaborating with others that have complementary skills on a joined venture. And now secondly by growing the company. I did consider dropping the product side and growing the consultancy side instead, but decided against it. Having scaled a few organisations in the past, I'm pretty sure I'd soon have to spend most of my time on sales, delegating most of the client work to less senior people. It's a bit of a bait and switch model with consultancies usually, and I don't like that. With just one employee, the equation is quite different: I can now take on small development projects that I had to reject in the past, and still personally ensure the problem is understood, the strategy is sound, quality is good and progress is swift. That wouldn't scale, but luckily it doesn't have to.

For the past few weeks, Gaurav Chauhan and I had been discussing on what should be our next step for progress and we decided to steer the wheel and expand. But really, how? Growth is exciting. It's a sign of progress, of reaching new heights, and of creating opportunities for others to join the journey. But let’s be honest—every time we talk about scaling up and building a larger team, a question lingers in the back of our minds: "How do we grow without compromising the culture we've worked so hard to build?" For me, #culture isn’t just about the perks or the office vibe. It’s about shared values, mutual respect, and the energy that keeps a team motivated and aligned. Here are a few principles I believe can guide us as we scale while preserving the atmosphere we cherish: 1️⃣ Hire for Culture Fit, Train for Skill: Skills can be taught, but attitude and alignment with company values are priceless. Every new hire should not just fill a role but also strengthen the team dynamic, especially in a startup. 2️⃣ Transparency at Every Step: Open communication fosters trust. Whether it's sharing goals, challenges, or changes, keeping everyone informed ensures we all move forward together. 3️⃣ Lead by Example: Leadership sets the tone. If we want positivity, collaboration, and accountability to thrive, it starts with us modeling those behaviors every day. 4️⃣ Preserve the “Why”: As teams grow, it’s easy to lose sight of why we started. Regularly reinforcing the company’s vision and purpose keeps everyone grounded and inspired. 5️⃣ Celebrate Wins, Big and Small: Expansion often means more challenges, but it also brings more victories. Acknowledging achievements keeps morale high and negativity at bay. #Scaling up doesn’t mean diluting what makes your team unique—it’s about amplifying it. With conscious effort and a shared commitment, we can create an environment where growth doesn’t just mean getting bigger but becoming better. Having said that, we're expanding our team and hiring for ALL POSITIONS! All interested candidates, do DM! #startups #growth #socialmediamarketing #teamexpansion

From Founder to Bureaucrat Mode 🚀➡️📋 Andrew Chen just dropped some wisdom on the shift from Founder Mode to Bureaucrat Mode, and while there aren’t any earth-shattering revelations, his insights are sharp and witty! 🔍✨ Entrepreneurial culture is fire 🔥, but let's face it—most companies are stuck in "Bureaucrat Mode." Here’s how you can spot it: 🔹 Endless committees for every decision  🔹 Meetings about meetings (seriously?!)  🔹 Projects get bloated instead of streamlined  🔹 Nobody owns a decision—consensus or bust! 🚫🤝 🔹 Personal initiative = instant side-eye 👀 🔹 Discipline for those who dare act solo  🔹 Progress checking involves a thesis defense 📊🎓 🔹 Over-complicated processes for simple tasks  🔹 Celebrating vanity metrics like it's a gold star 🏅 🔹 Rewards based on team size, not impact  🔹 Painfully long approval processes ⏳ 🔹 Risk-averse talk that stifles innovation 😬 Sound familiar? For many, way too familiar. 🙈 Sure, these rituals stem from good intentions—promoting collaboration and stability—but somewhere along the line, things went haywire. The original principles get twisted by folks who forget their purpose, leading to a self-replicating cycle of bureaucrats. Status gets tied to project scale and team size rather than actual impact. If winners hire winners and losers hire losers... then what do bureaucrats hire? You guessed it: more bureaucrats. 🌀 Companies obsessed with consensus and metrics inevitably attract those who thrive in that environment—until they hit a wall. Then it’s panic mode. 🚨 This cycle feels like the circle of life in tech: 1️⃣ Agile startup with bold founders pops up   2️⃣ They scale by hiring well-meaning managers   3️⃣ Market domination leads to IPO 🎉   4️⃣ Bureaucrats swoop in looking for stability (and shiny resumes)   5️⃣ The innovators bounce out; process takes over   6️⃣ Hello Bureaucrat Mode! 👋  And guess what? A new nimble startup emerges… again! Check out Andrew's full take here: Bureaucrat Mode (https://lnkd.in/dCZABbZX)

2 years into building Outset, I still consider myself a C+ manager. I don't believe early-stage founders need to be A+ managers. You're not even sure the company will exist in a year or two. For the record, I like to think I've been a good manager in the past. I've led teams of 10+ people with fairly positive reviews/results. But as a Founder at this stage, it's different. I spent a lot of time early on questioning myself and my management so far. I thought my focus and effort were off. So much that I sort of ranted about it to our lead investor, April Underwood. She shifted my thinking on this, though. She told me the best thing I can do for early employees is just make the company work. People don't join early-stage startups for stable careers with predictable title and salary growth, and regular one on ones to talk about their long term goals. They join them to move fast, learn a ton, and make a bet on the future. These people require far less managerial structure than those at established, mature companies. This isn't to say you shouldn't try to be a solid manager. It's just to say that not being a perfect one at this stage is really ok, and maybe even a good sign of your priorities. TLDR: at the earliest stages, the best thing you can do for your employees is to keep the company alive and even grow it.

Culture is BIG. It touches everything, & impact's everything & everyone. But...most startup HR & People teams are small...That's why we built this 👇 Culture Support = People & Culture consulting built (very) differently... 👉 Built for startup budgets 👉 Built for consistency & ongoing support 👉 Built to be there on-demand when you need us most 👉 Built to blend 'advisory' & 'hands-on' building to progress your projects We're so proud to be supporting some incredible companies already with this, including Gorilla - Energy data applications, Juro, Volt.io, Doist, INSHUR, Instant Impact, Bench Accounting, BKL and a few others... If you're a small people team operating in a startup/scale up business and you currently lack easy access to advice, coaching & resources, and the time to build & progress people & culture initiatives, check us out 👀 We have space & capacity to support a couple more orgs on some of the below areas! 👇