A well-run regular all-hands (every week or 2) can have a profound impact on a company. It can...
Set a cadence for the whole company
Hold departments accountable for delivering big wins on a regular basis
Force the leadership team to capture and summarize their thinking to the rest of the business on a regular basis
Build trust between all stakeholders
Help stakeholders across the company become aware of new developments and encourage people to jump in and help/align
And so much more!
VCs and smart money want to be pitched by the CEO.
Why? Because - as much as anything - they invest in the team running the company.
They need to feel comfortable that the leaders understand the operational details, have a clear and ambitious vision that is rooted in pragmatism and adaptability. They also need to like you.
Equally important - as the CEO/founder - you should want to meet any major investors in your round. It’s going to be one of the most important relationships in your life and the life of your company.
As a result, you can’t outsource the fundraising process.
Own it. Run it. Don’t stop until you drop.
How much money did you waste last month?
How much did the gap cost you?
The gap between what’s in your mind and the quality of your team’s day-to-day execution. How much lost business and lost customer confidence did that shortfall create?
How much did the indecision cost you?
Endless conversations trying to reach consensus. Endless research and analysis trying to find conviction. Going around in circles with your team. How much did you spend on salaries during that time? How much productivity have you lost from diminishing team morale? How much progress did your competitors make in that time?
How much did your bad decisions cost you?
Remember those days, weeks or months going down the wrong path and building the wrong thing? What was the price of leaving a bad impression on investors, partners, customers, employees, and more?
How much did that ineffective execution cost you?
How much did your ugly, broken, buggy, hard to understand, hard to adopt, hard to use, hard to love product cost you? How many customers landed on your home page but didn't understand your value props? How many couldn't be bothered finishing your signup process? Do you even have a signup process that doesn't require sales and engineering support? How many tried your product for a few seconds or even for a few days but then never returned? How much time, effort, and money did you spend trying to acquire those users only to see them walk out the door?
How much did those missed opportunities cost you?
How many sales didn't close? Which partnerships failed?.Which investors passed on investing in your business because they "just didn't get it"? What profits did you miss by not investing your time and money in other, better investments?
This is just a taste of the size and shape of opportunity cost.
All because you…
a) Hired that less effective employee
b) Avoided hiring that expensive advisor
c) Balked at the price of that better tool
d) Avoided making that hard decision
e) Put off that difficult conversation
Or countless other “cost-saving” or face-saving activities.
How much money did you waste?
How much money are you willing to waste next month? Next quarter?
Join the conversation about this on linkedin
I know it’s much easier said than done - but to build a successful startup you need to…
1. Ship product that solves a problem
2. Sell product and/or raise money
3. Use the funds to focus on your startup and hire help
If you’re not able to do the above then ether…
1. The problem you’re solving isn’t painful enough or real
2. Your hypothesis for the solution isn’t right
3. Your implementation of the solution isn’t good enough (this might also be because you’re trying to boil the ocean or your business model isn’t right)
4. Your go-to-marker tactics aren’t good enough
Don’t keep banging your head against the wall. Don’t quit. Figure out what’s going on and fix it.
This might involve some hard introspection, hard choices and a hard pivot (potentially into a new startup all together).
A large part of Startup success is rooted in momentum.
Why?
Because part of the defining characteristics of startups is that they are high-growth. High growth requires speed and compounding effects.
But why?
Because...
a) Software is relatively easy to create.
b) Software economics, flywheel effects, and VC funding dynamics mean that they often exist in a winner-take-most market.
c) Momentum and success attract momentum and success.
d) You typically have a limited runway (capital to spend) and need to maximize your outcomes to succeed at closing your next funding round.
This means at least 3 important things.
a) Competition will come for you.
b) Opportunity cost is typically your largest cost.
c) Smart investors also know all of this and look for it.
You need a healthy level of paranoia and hustle (but not recklessness and thrash).
Don't put meetings off to next week that you could have this week.
Don't let decisions linger.
Don't start and stop.
Take effective/efficient action.
Don't forget you are typically competing globally - you need to meet or exceed the best in the world - not just in your local market.
Build momentum. Maintain momentum. Use momentum to win.
Do you have a performance rubric for every function in your scaleup?
It should define what AWESOME looks like for every aspect of the role.
Here's a small taste example for a Senior Product Manager across "Fail", "Below Expectations", "Meets Expectations", "Exceeds Expectations" and "Total Rockstar" for the role aspect "Product Strategy Development"
Fail
Is unable to develop a solid narrative and roadmap for 1 squad despite help from manager. Does not work well with their team to refine the plan and or with leadership to get buy-in.un
Below Expectations
Is able to develop a narrative and roadmap for 1 squad with some supervision. Generally works well with their team and leadership to refine the plan but requires some assistance to get full buyin.
Meets expectations
Is able to develop a solid narrative and roadmap for 1 squad with no supervision. Works well with their team to refine the plan and works well with leadership to get buy-in.
Exceeds Expectations
Is able to develop a solid narrative and roadmap for 1 squad with no supervision. Assists/mentors others to do the same. Works well with their team and broader stakeholders to refine the plan and works well with leadership to get buy-in and push the status quo.
Total Rockstar
Is able to develop a solid narrative and roadmap for more than 1 squad with no supervision. Assists/mentors others to do the same. Leads/influences other teams and the org to refine their plans and and drive leadership decisions.
When things are misaligned across departments, product areas etc, the problem is not any particular decision/implementation but the misalignment itself.
You can spend all day trying to improve the specific implementations - but until you address the misalignment, things will continue to be broken.
There are no sacred cows.
Find inefficiencies, bureaucracies, pain, and suffering in your org. Highlight it and fix it. Don't take no for an answer.
Who's job is it? YOURS.
Most people don't understand how to identify common patterns to produce opinionated products.
They see the world as endless shades and believe that the complexity is not only inevitable and necessary, but also desirable and beneficial.
It's like looking at the rainbow and having the sense that there is infinite complexity and therefore infinite colors. Simplifying the spectrum seems impossible.
Great product managers look at a rainbow, draws bounding boxes and gives each part of the gradient a name. Yellow, red, green. blue etc.
They understand that by reducing the complexity into just a few well defined conditions, people will be able to more easily refer to parts of the color spectrum and accelerate everything from casual discussions, to artistic endeavors to even developing color science.
They also understand that rationalizing the complexity is not only possible, but highly desirable. Because they know that's exactly where value is created.
Thanks to cognitive inertia - it's so, so easy to make a pivot, change 1 or 2 of those things, and then accidentally forget to align the rest.
Essential things about your business can end up in an awkward, misaligned state. Part of your business has transitioned, and part of it has not.
A pivot can and should impact every aspect of your business. Brand, positioning, business model, pricing strategy, go-to-market tactics, product strategy, product UX metaphors, and more.
One way to make it easier is to create a migration strategy.
In 1 table, list every aspect of your business in each row.
In column 1, describe how you're currently handling that aspect of the business pre-pivot.
In column 2, described how you intend to adjust things as part of any kind of transitionary state.
In column 3, list how things will be done in the new post-pivot world.
You might be surprised how much can and will change.
For hints at what aspects of your business to list in each row, check out the business alignment stack I created last year.
Managing up (helping people above you in the org understand what they need to be doing and how they need to be interacting with you) is an essential part of being a great leader in any company.
However, it can often be quite difficult.
Why?
Sometimes, your leadership is simply and generally unreceptive to most new ideas or perspectives from anywhere (bad!)
Sometimes, the very thing you've noticed is a sore point (or a point of weakness) for your leaders - so they don't understand or appreciate the thing you are pointing out (blind spot!)
Sometimes, they might feel like the thing you're pointing out is simply "not your job," or you lack the context to make a coherent observation (who asked you??)
Sometimes, they might feel like you are selfishly advocating for your area/perspective/department at the expense of others - even if you might be objectively right (he's just biased!)
Sometimes, you simply don't have the authority to build consensus with your peers - so a decision never gets made.
Therefore, sometimes, the answer is that you need a 3rd party perspective (external contractor, advisor, mentor) to help.
Lean on them.
Distribution/go-to-market partners almost never work out the way you want. Incentives misalign, operationalization fails, days and months are spent figuring out the details.
Technology partnerships where you outsource large parts of your core experience to a 3rd party (particularly a b2c company!) introduce problems around roadmap, business model, IP ownership, and more
Instead, focus on...
a) Selling your own sh*t
b) Building your own sh*t
c) Customer/vendor relationships with proper b2b companies with discrete components
d) Affiliate partnerships with 3rd parties that can send you leads to your branded product and YOU own the customer
Everything else is likely to end up in a giant mess
For this reason, make sure your BizDev team is serving your product team's roadmap - not the other way around.
There are often situations where coworkers seem to refuse to do what you need them to do.
Often times this is simply because they don’t know HOW but are afraid to admit it.
You can pressure them, berate them, resent them all you like but - like getting water out of a stone - it’s simply impossible for them to do what you need them to do.
They can’t conceive of how to do it and/or they don’t have the skills or mindset to get it done.
In these situations you only have a few options
1. If they’re your boss and they have no self-awareness to take your lead or compensate with another hire: quit
2. If they’re your peer: Work around them or get them fired
3. If they report to you: Stop banging your head against the wall and do 1 or 2 of the following…
a) Get them a coach/help
b) Recognize their strengths and get them to focus them on those tasks while you hire someone else to do the other thing you need
c) Fire and replace them
Do NOT spend days, weeks and months thinking something will change if only you apply more pressure.
All you’re doing is frustrating everyone and wasting time.
Startups are rollercoaster rides of high highs and low lows. Sometimes in the same day!
There’s a lot of good ways for founders and operators to deal with these emotions.
A terrible way is to lash out at your team and become flaky and inconsistent with your engagement levels.
Show up, keep a level head, focus on the big picture, keep everyone moving forward.
As companies get bigger they often get bloated, slow, and lose the ability to deliver new value, quickly.
During times of market volatility, this kind of inefficiency can not continue. Speed, agility, and efficiency need to be restored to exit a downturn with accelerated success and growth.
But what are the key mistakes these companies make that lead to a breakdown of meaningful value creation and innovation and speed?
Here are 7 common deadly sins...
Poor context setting by the leadership team
Before any group of people can make good, well-aligned decisions, they first need to be on the same page. The larger the group gets, the more explicit, and well-articulated the shared context must be.
There are many forms of shared context. These include cultural values, definitions of what "great" looks like (for people, products, and processes), a vision for where the company is going, and more.
Many companies fail to create these (or fail to create good versions of them) and share them with the whole company.
Poor operationalization of shared context
In many cases, shared context documents are developed, but they are not integrated into the day-to-day operational cadence of the business. Onboarding, hiring rubrics, performance reviews, planning cycles, day-to-day meetings, and everyday decisions fail to use the framing and vocabulary of the cultural values, definitions of great, product principles, etc
Poor planning
Plans from leadership tend to be either a) too high-level or b) too tactical.
Plans that are too high-level leave too much room for ambiguity and don't help the team make tough tradeoffs. Things move too slowly and/or do not align to create meaningful short-term value.
Plans that are too tactical stifle innovation, decision making, and parallelism at the edges. Product managers and other leaders start acting as messengers instead of taking full ownership of their areas of responsibility. Good decision-making does not scale.
Poor org structure
Broadly speaking, there tends to be two bad ways that teams are organized.
a) Teams are split by function rather than by purpose/problem/mission. Product, design, engineering, and other key functions sit in silos that don't interact well together. Tribes form and collaboration stalls.
b) Teams are grouped into cross-functional squads, but the missions of squads are poorly designed such that there are too many cross dependencies between them. Clear lines of full-stack ownership are never fully established.
Poor role design and ways of working
Rather than build a better team, companies tend to hire more people in more specialized functions to compensate for the weaknesses of their existing team.
This ultimately diffuses accountability and adds communication overhead to everything. It slows everything down. It makes it hard to hold people accountable.
As a clear example, a product squad should basically only have 6 types of people. Product Manager, Product Designer, Engineering Manager, Product Marketing, Engineers, Data Scientist. Sometimes there's a need for 1 or 2 other specialist roles depending on the org/business.
No Business Analysts, Scrum Masters, Product Owners, Architects, QA, Customer Experience, etc.
Poor risk-taking
Classic innovator's dilemma quickly sets in. Decisions start to become incremental and new ideas tend to be too hard to digest or feel too risky to pursue. In some terrible cases, an "innovation" team is created to try to compensate. Fail. Innovation is everyone's job.
Piecemeal attempts to rectify
Rather than leadership taking bold steps to address all of the above (and more), they often avoid making hard decisions or rocking the boat too much. Changes to the business and the org tend to be too incremental. Often times it feels like it's no one's job to really fix the problem and building consensus for hard changes can be almost impossible.
What can be done?
That's a post for another day!
Everyone in Product Management (maybe also PMM, Design) in a big group meeting with the Head of Product (Optional CEO/CTO) to discuss company-wide, big-picture issues, cultural changes, and maybe some show-and-tell of big releases coming up, etc.
Optional opportunity for a product, design, PMM leader to share a best practice, a new idea, an industry trend, new cultural values, etc with whoever wants to attend. Informal, lunch-time slot that anyone can fill if they have something compelling to say to the group.
Opportunity for CEO, CMO, CRO, and CPO to share company-wide updates. Perf cycle updates, planning cycle updates, and offer Q&A.
Every PM (and maybe Design/Eng leads) in a group, meeting with the GPM, GDL, GEM to discuss business updates, group updates, perf cycles, planning cycles, where everyone’s at, any blockers, and what everyone’s up to in the coming week.
Chance to discuss any blockers, escalations etc. Also an opportunity to discuss career goals, performance etc. Tends to be less about the work and more about the individual. There might occasionally be "skip-level" meetings with their managers, manager.
PMs, EMs, Design leads meeting with the rest of their squad to update them on anything coming out of the Group meetings, the Town-hall, new missions, planning cycles, perf cycles etc.
The PM leads a meeting of all the key stakeholders involved in getting their roadmap/releases out the door successfully. Support, Sales, Marketing, Design, Bizdev etc. “Here’s where we’re at for this release, here’s what I need you to know, here’s what I need you to do for this upcoming release, where are you all at?”
PM meeting with whomever they need to meet with to get answers to their questions, flesh out their PRD, and drive alignment about an upcoming release. This can include…
Cross-squad coordination meetings to discuss with other PMs, Designers, EMs, etc any requirements/changes that might be needed from the parts of the product they shepherd
Deep-dive workshop meetings with sales, support, ops, etc to dig into key details for the next release (likely uncovered during the cross-functional syncs)
Meetings with the lead engineers for a given release to discuss scoping, technical details and ultimately handing off the PRD for technical planning
Meetings with designers to design screens and brainstorm on UX
Every 5-7 years or so, Silicon Valley and related tech hubs love to declare, "The End Times Have Arrived."
In the last couple of months, similar rumblings have been bubbling to the surface. With talk of rampant inflation, crashing stock market and crypto values, and increasingly nervous investors, startups are wondering what will happen next - and how to organize themselves to survive.
Here are some things to consider...
1. Recessions can be bad for traditional companies but can often be good for tech companies that represent greater efficiencies.
2. Some of the most important tech companies in recent memory were born during recessions - in particular, AirBnB and Uber come to mind. These companies offered customers a cheaper way to navigate the world while offering entrepreneurs another way to make some money on the side.
3. This effect can be seen in pretty much all sectors of the tech world, including medicine, commerce, logistics, healthcare etc. This is because, in lean times, companies can no longer afford to tolerate operating waste. Tech is usually the first, best answer to this challenge. In this scenario, tech products often move from being "nice to have" to representing an urgent solution to a pressing problem.
4. Making smarter, more effective decisions is key to surviving lean times and coming out the other side stronger and better than ever. This should be your internal mantra AND your pitch to customers.
5. You may need to shed staff and trim valuations in order to deal with tightening investor sentiment. However, this should NOT mean slashing your best or most essential people who help you make smarter, more efficient decisions.
6. Take this opportunity to invest in polish, scalability, efficiency of decision making, and high-quality execution to come out the other side with better products and more momentum than your competition.
Finally, I'd like to say that, despite doom and gloom prognostications from investors, these situations tend to be massively overblown. They tend to blow over in 6-12 months once everyone remembers that tech is well placed to benefit from downturns and that the sky, is in fact, not falling.
Stay focused, execute well, and deliver value, and you'll do fine.
Fundraising - like any deal - is like playing poker
There's no perfect answer. It's a game of negotiation and understanding the variables.
There's what's in your hand, what's in the river, and what's in the deck
Your product and metrics are what's in your hand. The reactions you're getting from investors are like the river (the cards in the middle of the table), the macro-economic conditions are like the deck in the dealer's hand.
Play each round. Pay close attention. Make the best deal you can.
How do you make sure the candidate you're interviewing is going to be a high performer?
Do they blame others for past failures? When you ask them how they get their job done, do they mention a lot of dependencies on other departments? Or do they express a sense of ownership and a 'pull-out-all-the-stops' perspective on their role?
Ask them how long it would take to do something. Are they talking about days and weeks? Or are they talking about months? Is their timing aggressive while also taking into account practical realities?
If it's a product manager, ask them to produce a PRD and brainstorm on it with you. If it's a designer, ask them to walk you through their portfolio. If it's a marketer, ask them to walk you through a number of their previous campaigns. Is their work fantastic?
Unless they express extreme discomfort with the bureaucracy of big legacy companies or the unscalable nature of agency work - these people tend to either work too slowly or be too comfortable with unscalable solutions to business problems.
Any transition from Startup to Scaleup must begin with a pitch deck.
Pitch your team - and educate new hires - as if they are your investors. Bring them along on the journey about the problem, solution, prioritization, cultural values, etc.
In this way, any required org changes move from being perceived as "change is scary" to perceived as principled, logical, obvious, and exciting!