This chapter will explore the application of a problem-structuring approach which synthesizes Vickers' concept of 'appreciation', Bateson's learning spirals, and Ackoff's approach to dealing with problems. This problem structuring approach involves three elements; explore, experiment, experience. The chapter describes, as an example, a case study taken from a United Kingdom unitary authority (anonymized for convenience) in which attempts were made to improve project performance using this approach. The organisation commissioned projects across multiple disciplines e.g. transport schemes, constructions, change programmes, business improvements using IT and bridge replacements, but was rated as poor at project management by successive internal and external reviews. Some conclusions are offered about the application of problem-structuring in order to learn lessons and promote good practice for the future.