Transparency: how much is too much?

Loneliness is a theme found in many leadership memoirs. While I can’t claim to have faced anywhere near the same magnitude of challenges as Ben Horowitz, this quote from his book The Hard Thing About Hard Things implies that this feeling isn’t reserved for billionaire founders or battlefield generals:

In life, everybody faces choices between doing what’s popular, easy, and wrong versus doing what’s lonely, difficult, and right.

Ben Horowitz

One way to relieve a portion of this leadership loneliness is by increasing the transparency shown by a manager to their employees. Part of the employee+manager relationship is helping the employee develop as a successor for the manager’s role. That means exposing the employee to the types of decisions that the manager makes–both big and small. Does the employee have capabilities required to do the job well? Perhaps more importantly, do they want to do this job? Greater transparency by the manager can help the employee learn more about the day-to-day reality of a more senior position, and can help the manager learn more about the employee’s readiness and willingness to take on greater responsibilities in the organization (those responsibilities could be functional or political).

Because many decisions that a manager faces will impact the employee, understanding the employee’s perspective can be an input to the decision itself. Asking the employee, “What would be a good outcome for you? What about for others on the team?” can help the manager identify blind spots in their perspective or approach the decision from a different frame of reference.

This leads to a dynamic where both transparency and trust must increase together for the strongest working relationship: one of partnership. The manager is sharing sensitive information with the employee. The employee is sharing candid responses. Both parties expect the other to treat the information with discretion. A high level of transparency without trust leads to a transactional, fleeting relationship — like a patron who will visit any shop that offers the best deal. A high level of trust without transparency is like the attitude of a pet toward its owner — always eager to take a ride in the car without knowing what the journey entails.

two by two matrix of transparency vs trust
Transparency and trust are closely linked attributes of a working relationship.

The risk of greater transparency by the manager is to create an expectation of an outcome that the manager can’t fulfill. For example if a potential organizational change — promotion, raise, prized assignment — is blocked elsewhere in “the machine.” This scenario will kick trust+transparency development in this relationship into a negative feedback loop, with the manager less likely to be transparent and the employee less likely to be trusting, both out of fear of inflicting further damage to the relationship, which of course is becomes self-fulfilling.

The manager’s challenge is not only to be selective when sharing the decisions they face with employees, but also to do so in a way that minimizes expectations they can’t deliver. One technique is for the manager to conduct decision reviews with the employee — after the fact — in the style described by Annie Duke in her book Thinking In Bets. This interaction should maximize the transparency and trust between the two parties without raising the risk of of a disappointing outcome for either.

So as with all things in life, there is such a thing as too much transparency from a manager to their employees. But when chosen carefully and supported by a high level of trust, moments of transparency can strengthen relationships and accelerate careers.

Photo by Ethan Sees on


Communicating goals: another lesson learned

Autumn brings hurricanes or falling leaves in different parts of the world, and for many of us it also brings annual goal-setting sessions. Here is a brief post summarizing a recent “aha moment” about the way leaders communicate these goals and how this communication style impacts results and team morale.

I’ll assume you are already a fan of the “Start with Why” principle popularized by Simon Sinek (if not, brush up here). When communicating goals: the Why must be clear, the What must be firm, and the How must be flexible.

Be Clear about Why

The underlying principle or strategy behind a goal is “the Why.” Each goal must be linked back to a core principle of the organization or a pillar of the business strategy. In organizations where the strategy is already well defined and understood throughout the team, articulating this link might seem redundant – if this is your team, congratulations. Larger, more complex organizations in the midst of a strategic transformation or “pivot” will benefit from a direct explanation linking the goal to the Why. Without linking the goal to the why, team members tasked with executing the goal can question its value and apply less effort, focus, and rigor.

Be Firm about What

Define the desired outcomes of the goal in unwavering terms. If the strategy, business model, and cash flow forecast require 15% margin expansion next year, state this explicitly in the goal. If there are hard deadlines about when the team must put pencils down and complete a project, lock in the dates. Directional and ambiguous goals (“improve,” “accelerate,” “expand,” “transform”) expose everyone to misalignment before, during, and after the work.

Be Flexible about How

Leaders who are inclusive and empowering (see Multipliers) expect the team accountable for achieving the goal not only to understand the problem best, but also to select the best approach to resolve it. In an agile approach, we expect to learn and adapt as the project evolves. Rigidly defining the methods and tools that a team must employ to achieve a goal risks disenfranchising them, or even missing the goal. If we knew all the answers already, how could the problem exist?

As you define and communicate your goals for next year, keep these principles in mind. If the goals aren’t clearly linked to the underlying strategy, ask for clarity. If the goals themselves don’t have firm definitions of how far and how fast, help to define them. And if the goal itself constrains the method of achieving it, push back for flexibility. Setting goals isn’t easy – and achieving them is even harder without clear, firm, and flexible communication.

You built a new feature. What should it cost?

No pressure, but the success or failure of launching new software capabilities can determine the financial health of your company. After months of investment in development, testing, and marketing, the potential payoff from landing new logos and expanding current client subscriptions is what you need to demonstrate growth to your current (and future) investors. Like everything else in life, packaging and pricing decisions are about making tradeoffs: in this case between the priorities of Product, Sales, Client, and Finance personas.

What do these personas care about? With apologies to Tolstoy, each unhappy team is unhappy in its own way, but it’s safe to believe the following motivations are true:

  • Sales wants to get paid
  • Clients want it for free
  • Product wants adoption
  • Finance wants accretive growth

Of course we could add complexity to these incentives, and you will likely face some of these complexities (and others) in your business. Does top line growth or profitability matter more to your investors in the pursuit of Rule of 40 growth? Does new logo acquisition or current client expansion matter more to your industry analysts? Does your Sales comp plan pay the same commission rate on expansion sales as new sales (i.e., is the cost of sales equivalent)? Is your product team incented on feature adoption, or build quality? Is the new feature a strong positive differentiator vs competitors, or ‘table stakes?’ And more. For now, let’s keep a simplified view and compare a few practical options to launch your new feature.

Bundle it in

In this scenario, include the new feature at no additional charge with an existing product or edition without changing the list price. Current clients already using the edition that contains the new feature will ‘just get it’ when they receive the new release. Sales will get paid when new clients purchase this edition, or when existing clients upgrade from a lower-tier edition. Finance will likely yawn unless the new feature generates significant market share growth.

This option is best suited for situations when the feature is ‘table stakes’ and restores parity to competitors’ equivalent offerings, or when adding the feature to a top-tier edition increases the perceived value and drives upsell among the existing client base. If your competitive intelligence has shown low win rates and poor perceived value of an existing edition, and your test clients showed relatively low willingness to pay for the new feature on a standalone basis, this option might be your best choice.

Raise the price

When the new feature is highly differentiating and sample buyers demonstrate a high willingness to pay, set a higher price for bundles/editions that include it. Current clients will likely be ‘grandfathered in’ to start using the new feature before a higher price kicks in at renewal. Client Success and Product Marketing teams will use this preview period to gather feedback and testimonials to validate the expected value of the new feature. These proof points will help to diffuse any resistance to the increased price from new buyers. Both Sales and Finance teams will be thrilled by the higher transaction value, assuming that win rate and deal cycle length (key variables in the Sales Velocity Equation) don’t drop concurrently.

Give them the option

A middle-ground option makes the new feature a paid add-on to existing products or bundles. This configuration can get Sales teams excited to sell something new to existing customers who are mid-term in their contract (and retire some quota in the process). Be careful that the new feature, with a value prop of its own, doesn’t get “thrown in” at a discount to close deals — undermining the Product Marketing team’s ability to validate the market’s willingness to pay, trashing the Finance team’s margin forecasts, or artificially depressing the Product team’s adoption trends (if the feature is ignored by buyers who were indifferent to it in the first place). A paid add-on will require a new “SKU” in your catalog and add complexity to provisioning/shipment and run-books for your Ops teams. If your organization has immature Product Launch processes, make sure to give these teams 4-8 weeks notice so they can review, modify, and test their procedures to support the new feature as a paid add-on.

But wait, there’s more

Launch planning can feel like a tug-of-war between numerous groups with competing priorities and often misaligned incentives. While it’s impossible to predict how your clients, prospects, and competitors will react to your launch, the concepts above might help you make a more informed decision on how to package and price the new feature.

For more information about packaging, pricing, and product launch, try these resources:

I spend most of my days thinking about packaging, pricing, monetization, and the lead-to-cash cycle for a B2B SaaS business. I’m open to questions, feedback, challenges, and new ideas from people in the same situation – please leave a comment or contact me directly.

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Compared to What?

Life is about making choices, and those choices have consequences. In business, leaders are constantly making choices: which projects to prioritize, which candidates to hire, which vendors to select, which targets to acquire, which virtual background to use in the next video conference.

If business is a test, many leaders under pressure often treat these decisions as true-false questions rather than multiple choice. They look at each potential solution as soon as it’s visible, and decide “yes or no:” if yes, stop looking for alternatives; if no, move on to the next yes-no decision.

Another approach is to collect potential solutions and evaluate them as a set. What are the comparative strengths of each? How could the leader construct a hybrid solution by combining the best components into a single solution? Can one long-shot solution become negotiating leverage against the incumbent? And finally, have you evaluated your potential actions against the alternative of “do nothing” ?

Maybe take a little longer to understand the alternatives?

But don’t dawdle: according to some research on optimal decision making, collecting too much information before making a decision can be worse than making a snap judgement using intuition alone.

Once a decision has been made, is a leader willing to change course if the results don’t come through as expected? A common bias is the sunk cost fallacy – the cause of “throwing good money after bad.” After making a decision, re-assess the path you are on versus the alternatives that are still available. Net of additional switching costs, can what you have learned since the initial decision lead to a better outcome with an alternative solution?

Leaders face a barrage of decisions each day. My intent is that the techniques outlined above help you achieve better outcomes from at least a few of those decisions. Please use the comments to provide your feedback and questions.

TIL: the agenda is a suggestion

Today I Learned

Meetings are a request for scarce resources, made days (or weeks) before the event. In the time between the meeting request and the event, new information appears and relationships evolve.

What this means to me

Any discussion should include the most important topics that the attendees need to address at the time of the meeting, not only those proposed in the agenda when the meeting was scheduled. If we don’t, we are wasting scarce resources, denying ourselves the current truth, and ultimately weakening our relationships.

Putting this knowledge to work

After reviewing the proposed agenda for a scheduled meeting, raise what I believe to be the most important topics to the discuss with the other attendees, and allow the group to decide how to devote the remaining time. Follow up 1:1 afterwards as needed to discuss the most important topics.

Two quick examples

  • Arriving at a standing monthly meeting, we review the pre-defined agenda and standard “status deck.” There are critical resourcing issues that emerged since the last meeting that aren’t on the agenda but are impacting the team’s rate of progress, so I ask the team is we can spend 10 minutes during the current meeting discussing that issue or to find another time before the end of the day that’s more convenient .
  • When I get a vague or empty meeting request from a person I don’t work closely with, I decline the meeting request and politely request clarification on what they want to achieve with the discussion. Sometimes a quick phone call can help soften this reply as it’s somewhat unusual in corporate culture.


If you have questions or feedback about this idea, or about my new short-form post type “TIL,” please leave a comment below.

TIL: the stress comes from guessing

Today I Learned

Anxiety and stress in our most important relationships arises from guessing what others want from us, and from guessing how we should “show up” for them.

What this means to me

During intense conversations at home or at work, when I am guessing what the other person needs from me I feel anxious and physically stressed. This causes the conversation (and therefore the relationship) to degrade in a few ways:

  1. I’m no longer listening fully to the other person because I’m distracted by thinking about my own feelings and needs.
  2. In a state of “arousal” (fight-or-flight) my listening and attention will get even worse.
  3. The other person, seeing me in a stress state, could react to that with their own stress response, amplifying the anxiety and stress of the conversation.

Putting this knowledge to work

Just ask the other person what they need, and to tell them what you need, so that we can show up for each other in the most helpful way and avoid the stress of guessing.

Two quick examples

  • When my spouse starts telling me about a difficult part of the day, I can say “that sounds tough…do you need strategy or sympathy from me right now?”
  • When I am talking with someone on my team about a challenge we need to solve, be explicit about my expectations: “I just need to talk through this scenario with someone – can you help poke some holes in my hypothesis? If there are any actions for you afterwards, I’ll be specific.”


If you have questions or feedback about this idea, or about my new short-form post type “TIL,” please leave a comment below.

TIL: Hack the half-second

Today I Learned

The human brain takes up to half a second after receiving sensory inputs to apply judgments, cognitive biases, and labels.

What this means to me

A core personal development theme for me is to become less reactive. Instead of classifying an event as bad (or good) and labeling the person who “caused” it as incompetent (or amazing), I’m trying to delay those sub-second reactions.

Putting this knowledge to work

Daily practice to delay my reaction between an observation and a response (meditation helps here). Change my genuine reaction to an event with curiosity: see things as neither good nor bad, just things to explore and understand. Don’t react at all to things that are out of my control (yes, this has echoes of Stoicism).


If you have questions or feedback about this idea, or about my new short-form post type “TIL,” please leave a comment below.

How much can we achieve? Leadership isn’t enough

It’s that time of year again: most companies are pushing hard to close the final quarter of the fiscal year while simultaneously planning the budget and strategic objectives for next year. Depending on the type, size, and maturity of your business, this exercise could include anything from a rigorous, zero-based, quantitative analysis of global operations to a white board session over a beer. Or maybe not: Basecamp doesn’t plan more than six weeks ahead. Most likely, your experience involves too many revisions of painfully formatted spreadsheets that will be forgotten in a few months when the reality of daily business sets in.

Regardless of the mechanics of your planning process, the fundamental question is: how much can we achieve?

In many organizations, the answer to this question starts and ends with leadership. But when growth requires broad adoption of new systems, behavior change by the end users of these systems matters as much as, or more than, leadership capacity. Let’s look at why this matters, and what you can do differently in this year’s planning cycle to incorporate the concept.

Leaders think leadership is important. Whether it’s self-preservation or cognitive bias, many leadership teams will over-weight their role in driving change. I’m not endorsing the leaderless organization fad, and I believe it’s essential to sanity-check the number of strategic objectives and special projects assigned to each leader (in addition to his or her “business as usual” responsibilities) when building an annual plan. Even an Agile approach to program and project management, with more frequent interrogation of outcomes, risks, and blockers, can leave leaders overwhelmed. When a single leader is overloaded, delays and dependencies can put an entire program at risk. When the organization is capable of a high rate of change without enough effective leadership capacity, employees feel disengaged and top talent starts to look elsewhere. So if we’ve established that leadership capacity matters, why isn’t that enough?

Sustained improvement happens when a new, better thing happens more often than the previous, worse thing. Even in highly technical, capital-intensive industries, measurable changes in performance only occur with adoption of new solutions. Software teams can ship new features, and if users don’t adopt those features, the users don’t realize the benefits, no matter how many times in a row you say the word “done.” Managers can train teams on new procedures, and if those employees don’t perform their work differently, the same defects, inefficiencies–even accidents–will persist. Marketing teams can crank out more content, and if sellers don’t change the way they engage with buyers…you get it.

Therefore, in addition to a “top down” assessment of leadership capacity across projects, take a “bottom up” view of behavior changes during your annual planning cycle. Look across your portfolio of projects: which roles, or individuals, in the organization will have to sustain behavior change for the projects to succeed? Are we asking too much of the same people?

Here’s a hypothetical example from a fictional software company:

  • HR leadership plans to change the performance management process, using a new online tool
  • Marketing leadership plans to change the content management system, including how inbound leads are routed to Sales
  • Operations leadership plans to change the quote to cash process, including a new set of contract templates
  • Sales leadership plans to change the compensation structure, with different payouts for new logos vs account expansion
  • Product leadership plans to introduce a new self-service subscription feature as part of the next major release

From a top down view this set of projects will require cross-functional coordination, however, no single leader will be overloaded with responsibilities. Great, all set, let’s get started–right? A bottom up view of the behavior changes required for these projects to generate results, however, reveals that Sales Managers will be overwhelmed by requests from different project leaders to work differently. It is much better to identify this risk during the planning cycle than in the mid-year review, when each project leader is scrambling to understand–or worse, to blame the Sales Managers–why they are not hitting their numbers.

Leadership matters. But without behavior change that fuels adoption, results don’t stick. Try this approach in your annual planning cycle to see if it generates a greater rate of improvement–and leave a comment below with any questions or feedback.

This phrase shows you’re a disengaged manager

It’s another busy week for you and your team, and you are feeling very productive while working through your action list. You write a concise email to a few team members with the intent of delegating work for the coming week, and cheerily close with this line:

Let me know how I can help.

— what you said to your team

Those six words have just sent a powerful, yet subtle message to your team:

I want to maintain the appearance of supporting you, but I’m not actually engaged in your success.

— how your team perceives you

Genuine support arises from setting clear direction, being accessible to engage, and providing effective coaching. “Let me know how I can help” creates a veil of accessibility, while placing the burden entirely on the team to understand the direction and seek out the manager’s support. The irony of the disengaged manager is that the team members who could benefit most from support — those with the greatest need for direction and coaching — have the largest barrier to receiving support.

After clearly establishing the mission and purpose for the team (“the why”), setting clear direction means that you’ve defined both what to do and how to do it. To use a trivial example: when my family works together to prepare dinner, the why is an expression of our values (satisfy our nutritional needs, self-sufficiency, appreciation of diverse cuisines, etc.). The what is a set of tasks and recipes that comprise the meal, and the how is a standard of quality and steps to follow so that no one gets hurt and the meal is tasty.

In a work environment, the manager needs to discern whether the team member needs help with what to do or how to do it (or both). Asking questions (“Tell me how…”) and reviewing draft work product (“Show me what…”) are effective techniques to assess any gaps. The manager should be doing much more listening than talking in this interaction. The table below suggests some practical steps for the manager depending on each team member’s situation.

It’s not your team members’ responsibility to let you know how you can help them. As an engaged manager, genuine support arises from:

  • Setting clear direction by expressing the mission and purpose of the team’s work in clear and compelling terms (“the why”)
  • Being accessible to engage by scheduling regular 1:1 checkpoints and leaving blocks in your schedule when your team can find you for informal, ad hoc collaboration
  • Providing effective coaching by assessing whether each team member understands what to do and how to do it, and then following through with the right type of support for the scenario

How does this approach fit with your team culture? What’s stopping you as a manager from engaging more with your team? What’s an even better way to provide genuine support? Leave a comment below…

Delegate everything

All of the time management books, blogs, lectures, and videos you’ve already seen boil down to two concepts:

  1. Prioritization: Is the right work getting the right amount of resource overall?
  2. Delegation: Is the active work being done with the right leverage in the organization?

Since “the right work” is always a mix of urgent, strategic, cash-generating, compliance-driven, and internally-focused tasks, the list can seem nearly endless. For that reason it can be more useful to flip the question: rather than asking “what work should be done today?” instead think about prioritization as deciding what work should not be done by anyone in the organization.

By extending the same logic to a manager’s own work list, think about delegation as deciding what work should not be done by the most senior person on the team.

Recently I’ve attempted to take this principle to the extreme by challenging myself to delegate everything. Does this mean that each day I do…nothing? Of course not (although I still aspire to). It does mean that for each new task that passes the prioritization filter above, I ask the following questions:

  • Who on my team has already demonstrated the capability to complete this work successfully?
  • Who on my team could take this work as a development opportunity?

Then I will spend a few minutes with these folks and review the “what by when” to ensure that the deliverable, the ready date, the standard of quality, and the approach are clear.

Now in many cases the team member(s) are not yet ready to take on the new work, either because the capability gap is a bit too large, or other work must get done within the available time. Whenever possible, it’s best for the team member to attempt the work even if the manager completes it, both for the experience and to capture some specific feedback that supports his or her professional development.

Regardless of whether the team member completes the delegate-able work, both the manager and the team member benefit:

  • More frequent calibration on the team members’ capabilities and gaps to the next level
  • More frequent and more specific feedback
  • More visibility into the “day in the life” of the manager, which helps to increase transparency about the present (“what does she do all day?”) and the future (“do I really want that job one day?”)
  • More effort applied at the highest point of leverage in the organization – meaning that work is done by the most junior person who can complete it successfully. This creates capacity for both senior and junior resources to tackle more challenging work

Delegation is difficult because when done properly, there is a genuine risk of failure for both parties. By attempting to delegate everything, you are flipping the question from “what can I delegate?” to “what can’t I delegate, and why?”

For more information on delegation, time management, and organizational design, try these books by Eliot Jaques, Andy Grove, and Peter Drucker.