Setting Expectations

The best way to establish a productive & stress-free relationship of any kind is to set the right expectations. But it’s tempting at times not to have the discipline to appropriately set expectations at the beginning. I’ve experienced the anxiety of mis-setting expectations on the receiving and the giving end, which has led to a lot of discipline with my own expectation setting.

Good expectation setting examples in the real world

For customers.

At onefinestay, we try to set expectations at the onset for how a customer is likely to experience the service. This doesn’t mean playing to the edge cases - but what we genuinely believe is likely to happen in the host or guest experience. For the host, who is offering their home to guests while their out of town, this means investing the time upfront to ensure understanding of wear-and-tear, what happens in the event something goes wrong in the home during a guest stay, and how we respond - timelines, who pays - should that something actually cost money or time to remediate. We also try and set expectations to the best of our ability around likelihood of bookings at various price points and times of year. This means investing the time up front to present hosts with actual data from our business (e.g. if you live in a 3-bedroom in Chelsea and will be gone this summer, we will pull comparable homes from both the market and our own internal host community and speak to performance - and leave this behind after our first meeting) so an informed choice can be made. Hosts are always evaluating an alternative, even if it’s just leaving their home empty, and we only want to enter into situations where we believe we can provide the killer product. 

For guests, this means doing everything we can prior to the booking and arrival stage so that they know what they’re buying. We’re building out a new accommodation category - a home with hotel-style benefits, so sometimes expectation setting is as fundamental as ‘be aware - you are booking a real person’s home!’. We also try and list all of the home specific quirks transparently on the home listing page in a ‘home truths’ section - if a cat lives in the home and you have allergies, you’ll know this upfront.  

For hiring.

Jerry Colonna says that what employees need most to succeed is clarity. Amongst other things, this means a well written job spec that reflects the actual work required for the role. I try when interviewing to ensure a prospective hire knows what they are getting into by asking ‘what’s your understanding of the day to day role’? Lastly, it’s really important to talk about how things like typical office hours, expected out of hours responsiveness, promotion, and pay cycles work within a specific environment - this varies a lot between organizations so is best to expose fully. I can still remember countless evenings when I was a banker, work done for the day, not knowing whether or not it was OK to go home and get some rest.

For special cases, I loved Sheryl Sandberg’s story in ‘Lean In’ about Cynthia Hogan, who was asked by Vice President-elect Joe Biden to join his staff after taking time off to have kids. Instead of declining a role due to her presumption of the late nights required, she flagged this as a concern early to which Biden responded ‘well, you have a phone and I can call you when I need you after dinnertime’. Cynthia exposing her situation upfront led to her boss resetting his own expectations so he could bring in the right talent for the job. 

For investors.

Do you know the return or liquidity timing expectations of your investors? Even within the VC world, I’ve observed a surprising amount of variation in investment performance expectations - some funds will steer the business towards ‘$1bn or bust’ outcomes, whereas others would prefer safer bets for more conservative returns. Some funds are investing purely to maximize financial return, others have non-monetary objectives. And, fund lifecycle will play a big part as well - are you the last deal in an aging fund with a lot of unrealized investments or the first deal in the next fund with a proven track record? This more than most other aspects of business can dictate strategic options down the line. 

For suppliers.

For suppliers & service providers, discussions often get mired in complicated contracts drafted in legalese. This can make the more human challenge of expectation setting more difficult. In some cases, contracts can be modified to reflect the intent of the agreement. If not, I always establish a clear ‘plain English’ understanding, in writing, of how I expect things to unfold if not everything goes as planned, and ask for confirmation of agreement in writing, too. Or I find a supplier with a more robust contract. At onefinestay we’ve found this particularly valuable with maintenance providers - e.g. plumbers, exterminators, general contractors. It was illuminating to contrast what certain suppliers would say over the phone vs what they’ll agree to in a contract. 

Causes and remedies

In my experience there are two root causes of mis-set expectations - one innocent and the other more insidious. The innocent cause of mis-set expectations is a misunderstanding - language is complicated and conversations can often conclude without both sides in full agreement. To combat this, I often find myself repeating certain salient points to underscore their importance (even at the risk of redundancy), and sending an email recap afterwards. I also always try and practice what Thich Nhat Hanh calls ‘language of the world’ - when in doubt, use the simplest word or phrase possible to agree a point. Good communication is about understanding, not demonstrating an advanced command of a language.  

The second root cause - and one that I’ve certainly fallen victim to from time - is a glossing over specific details because of fear losing the ‘deal’ - the investor, the hire, the revenue. So we kick the can until a future day of reckoning, when either we get lucky because an outcome we’ve alluded to comes to fruition, or things fall apart and we have to pick up the pieces. Needless to say: this isn’t a good outcome for the expectation setter and can leave a permanent feeling of disappointment with the other side. It’s also a great way to stress yourself out in the meantime, which isn’t a good way to live. There are a number of personal development strategies for dealing with fear. And as my old boss used to say, part of the battle is being completely comfortable with any potential outcome so that you’re not afraid to lose the deal - whatever that deal may be. 

Parting thought 

Proper expectation setting means working through fear to arrive at a transparent outcome for both sides. It’s not always the most expedient thing to do, and can sometimes even feel awkward. Have the discipline and patience to do it right - it has certainly made a difference in my life.