Office Hours #5 — Underpromise, Overdeliver

Common trait that stands out among top performer.

This is the fifth installment of the weekly Office Hours series, where I explore common questions raised in discussions with engineers within and outside of Xendit.

When I look back on all of those that I consider top performers in my career, there is one common trait that stands out among them. That is the ability to effectively manage expectations. I love the phrase “Underpromise, Overdeliver” because it neatly captures the spirit of this idea. The best performers are able to execute this from a task level up to a company level to provide guidance on top and bottom line numbers. This skill serves as the foundation of the trust in that individual because one of the key aspects of trust building is honoring commitments and extending to everyone, including (and especially) the executives.

Below, I’ll provide some practical steps to adopt to harness this powerful skill:

1. Set expectations explicitly, achieve buy in and alignment
2. Allow for margin of error, include buffers
3. Report regularly
4. Be proactive in adjusting expectations, disappoint early
5. Reflect and improve estimation and communications

Let’s dive in

Set Expectations Explicitly

The most frequent blocker that I’ve seen in adopting this practice is not having clear, explicitly defined, and documented expectations. The second most frequent blocker that I’ve seen is not having explicit buy in and alignment on those expectations. One party may believe that there has been agreement while the other party believes that the expectations are still being negotiated.

Practically, I recommend the following:

1. Have the party that is expected to deliver write a document that clearly defines the scope of work, definition/measurements of success, and timelines/milestones to hit
2. Have the stakeholder who expects the work to review, give feedback, and explicitly sign off on the document
3. During check ins, bring up the document and discuss progress relative to the document. If anything needs to be changed, have both parties make suggestions and agree to any edits.

This document will then form the basis for future discussions and to ensure scope doesn’t creep and goalposts don’t get moved without another explicit discussion.

Allow for Margin of Error

Despite our best efforts and intentions, plans will often go off track for a variety of expected and unexpected reasons. We know colloquially that “Shit Happens”. What top performers do really well is having the ability to estimate the impact of known unknowns and unknown unknowns.

For known unknowns, top performers will have a variety of fallback options and they will not rely on a single “Plan A”. This ensures that when things inevitably go wrong, the entire delivery is not derailed and original expectations still have a chance of being met.

For unknown unknowns, top performers will have a great sense of how much buffer space to include in their expectations. Doing this well is much art as it is science and I believe that it is an acquired skill with experience. Too little buffer risks not giving the delivery team enough time to recover if something unexpected happens. Too much buffer risks additional negotiation cycles with the customer/stakeholder which can eat into valuable delivery cycles.

Report Regularly

Reporting regularly and having granular and measurable milestones will give the delivery team a good sense of whether the original expectations are still on track. Picking the right reporting cadence depends on the stakeholders as well as the time frame of the project. For external stakeholders, there may only be a few opportunities to meet and demonstrate progress before the final deliverable is expected. For year long initiatives, meeting once a month is reasonable but for monthly initiatives, meeting weekly is likely more appropriate.

The goals of reporting should be:

1. Maximize chances of discovering risks to the original expectations so that they can be adjusted as soon as possible
2. Allow for incremental adjustment of the expectations as new information arises (e.g. customer needs change)

Proactively Adjusting Expectations

No one likes to be disappointed but in the context of managing expectations, I’ve found that it’s always better to disappoint early than to drag it out and incrementally move the goalposts. The latter has the potential to completely shatter trust in the long term and can be unrecoverable.

Practically, I recommend that as soon as there is an indication that a few milestones or the overall target cannot be met, start with flagging the customer/stakeholder that there are risks to the original expectations and come up with a conservative new proposal that the delivery team has a high confidence interval in. It’s important to be conservative and to disappoint as much as possible upfront because it will also set the delivery team up for success. It means that they will have a higher chance of overdelivering.

If and once this new proposal is accepted by the stakeholders, then the work of aiming to overdeliver begins again. A cautionary tale, I’ve seen many cases of delivery team leads who opt to chase their losses instead of cutting them and who wind up burning out their team as well as disappoint their customers. The absolute worst of both worlds.

Reflect and Improve

This is a step that is often overlooked as teams are in a rush to deliver. Taking the time to reflect and evaluate how successful the team and its leaders are at setting and managing expectations is a key for long term success. The team should assess all of the above, starting with how clearly expectations were set and how buy-in was achieved. The team should assess how many contingency cases were planned for and what unknown unknowns occurred. These can then become known unknowns for future efforts.

Conclusion

Delivery teams are often stretched to their limit to hit aggressive targets and timelines. Stakeholders and customers are demanding and growth is a justification for moving quickly. What I’ve seen is that in order to achieve long term growth, delivery teams and their leaders need to strengthen their ability to reduce negative surprises and maximize positive surprises for their stakeholders. This forms a powerful foundation of trust which gives those teams and leaders great negotiating power with stakeholders and customers and most importantly, sets their teams up to overdeliver. Chasing impossible deadlines for a fear of disappointing stakeholders just to inevitably miss those deadlines only leads to lost trust and demoralized teams.